An-Xin Wu

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines

Co-reporter:Xia Wu, Xiao Geng, Peng Zhao, Yan-dong Wu, and An-xin Wu

Organic Letters September 1, 2017 Volume 19(Issue 17) pp:

Publication Date(Web):August 23, 2017

DOI:10.1021/acs.orglett.7b02182

The iodine-catalyzed catalytic formal [3 + 3 + 1] cycloaddition for the preparation of a seven-membered O-heterocyclic ring is presented, which is an achievement of methyl and carbonyl group reactivity of 3-methyl-5-pyrazolones to forge the Csp3–O bond. This novel protocol provides a straightforward and efficient access to structurally diverse fused O-heterocycles through an iodine-catalyzed iodination/Kornblum oxidation/oxidative coupling/C–O bond formation cascade reaction. This approach demonstrates the unprecedented concurrent realization of the unique reactivity among the methyl, methylene, and carbonyl groups in 3-methyl-5-pyrazolones for the construction of 2,3-dihydrooxepine rings. Moreover, a broad substrate scope displays a graceful diversity-oriented synthetic approach.

Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids

Co-reporter:Jia-Chen Xiang, Zi-Xuan Wang, Yan Cheng, Shi-Qing Xia, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu, and An-Xin Wu

The Journal of Organic Chemistry September 1, 2017 Volume 82(Issue 17) pp:9210-9210

Publication Date(Web):July 28, 2017

DOI:10.1021/acs.joc.7b01501

A practicable quinoline synthesis from aniline and two amino acids was developed for generating a wide range of quinolines with high efficiency and diversity. Thus, it facilitated the creations of pharmaceutical derivatives, photochemical active compounds, and challenging scaffolds. The concept of using two amino acids as heterocyclic precursors has been raised for the first time. Mechanistic studies revealed that I2 enabled decarboxylation, oxidative deamination, and selective reconstruction of new C–N and C–C bonds processes.

Acid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether

Co-reporter:Kai-Lu Zheng, Min-Qi You, Wen-Ming Shu, Yan-Dong Wu, and An-Xin Wu

Organic Letters May 5, 2017 Volume 19(Issue 9) pp:

Publication Date(Web):April 19, 2017

DOI:10.1021/acs.orglett.7b00769

A novel one-pot reaction has been developed for the efficient synthesis of pyrrolo[2,1-a]isoquinolines and 1-dearyllamellarin core from (E)-(2-nitrovinyl)benzenes and azomethine ylides generated in situ. This strategy provides a concise total synthesis of the lamellarin core and lamellarin G trimethyl ether using electrophilic substitution and palladium-catalyzed Suzuki–Miyaura cross-coupling reactions.

Acid-Promoted Multicomponent Tandem Cyclization to Synthesize Fully Substituted Oxazoles via Robinson–Gabriel-Type Reaction

Co-reporter:Rong-Rong Zhou, Qun Cai, Deng-Kui Li, Shi-Yi Zhuang, Yan-Dong Wu, and An-Xin Wu

The Journal of Organic Chemistry June 16, 2017 Volume 82(Issue 12) pp:6450-6450

Publication Date(Web):May 19, 2017

DOI:10.1021/acs.joc.7b00763

An acid-promoted multicomponent reaction for the synthesis of diverse fully substituted oxazole derivatives from simple and readily available arylglyoxal monohydrates, nitriles, and various C-nucleophiles has been developed. This protocol features wide functional group diversity which is capable of installing 4-hydroxycoumarin, 2-naphthol, and 1,3-cyclohexanedione motifs to oxazoles. Mechanistic analysis indicates that a classical Robinson–Gabriel reaction served as the key step for this tandem transformation.

A C–H Oxidation/Two-Fold Cyclization Approach to Imidazopyridoindole Scaffold under Mild Oxidizing Conditions

Co-reporter:Jia-Chen Xiang, Zi-Xuan Wang, Yan Cheng, Jin-Tian Ma, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu, and An-Xin Wu

The Journal of Organic Chemistry December 15, 2017 Volume 82(Issue 24) pp:13671-13671

Publication Date(Web):November 24, 2017

DOI:10.1021/acs.joc.7b02448

An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through the C–H oxidation/two-fold cyclization reaction of methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize the efficient oxidation of C(sp3)–H bonds, while suppressing overoxidation of the intermediate and ensuring the cross-trapping of two in situ generated acylimine intermediates.

I2-Promoted Povarov-Type Reaction Using 1,4-Dithane-2,5-diol as an Ethylene Surrogate: Formal [4 + 2] Synthesis of Quinolines

Co-reporter:Xia Wu, Xiao Geng, Peng Zhao, Jingjing Zhang, Xingxing Gong, Yan-dong Wu, and An-xin Wu

Organic Letters April 7, 2017 Volume 19(Issue 7) pp:

Publication Date(Web):March 16, 2017

DOI:10.1021/acs.orglett.7b00361

A highly efficient I2-promoted formal [4 + 2] cycloaddition has been developed for the synthesis of 2-acylquinolines from methyl ketones and arylamines using 1,4-dithane-2,5-diol as an ethylene surrogate. Moreover, the investigation of the mechanism suggested that this reaction occurred via an iodination/Kornblum oxidation/Povarov/aromatization sequence. It is noteworthy that the arylamine substrate also played an important role in promoting the reaction.

Diamination/Oxidative Cross-Coupling/Bicyclization of Anilines and Methyl Ketones: Direct I2-Promoted Synthesis of 1,2-Fused Oxindoles

Co-reporter:Jingjing Zhang, Xia Wu, Qinghe Gao, Xiao Geng, Peng Zhao, Yan-Dong Wu, and Anxin Wu

Organic Letters 2017 Volume 19(Issue 2) pp:

Publication Date(Web):January 4, 2017

DOI:10.1021/acs.orglett.6b03636

An I2-promoted domino bicyclization approach via multiple sequential C–H functionalization was serendipitously discovered for the synthesis of 1,2-fused oxindoles from methyl ketones and anilines. This approach was optimized, resulting in a concise and atom-economical approach for the one-pot construction of 1,2-fused oxindoles from methyl ketones and anilines rather than using preexisting indolin-3-ones or indoles. Mechanistic studies revealed that the key step involved an oxidative cross-coupling between in situ generated phenylglyoxal and α,α-diaminoketone.

Temperature-Controlled Base-Promoted Cyclization for the Synthesis of 2-Amino-4H-benzo[d][1,3]thiazin-4-ones and 2-Thioxo-4(3H)-quinazolinones

Co-reporter:Zhi-Wen Zhou;Feng-Cheng Jia;Cheng Xu;Shi-Fen Jiang; Yan-Dong Wu; An-Xin Wu

Asian Journal of Organic Chemistry 2017 Volume 6(Issue 12) pp:1773-1777

Publication Date(Web):2017/12/01

DOI:10.1002/ajoc.201700443

AbstractA base-promoted and highly selective temperature-dependent tandem oxidation/decarboxylative cyclization of isothiocyanates and isatins has been developed. This method allows the chemodivergent synthesis of 4H-benzo[d][1,3]thiazin-4-ones and 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones in moderate to high yields.

A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement

Co-reporter:Zhi-Wen Zhou;Feng-Cheng Jia;Cheng Xu;Shi-Fen Jiang;Yan-Dong Wu

Chemical Communications 2017 vol. 53(Issue 6) pp:1056-1059

Publication Date(Web):2017/01/17

DOI:10.1039/C6CC09376K

An efficient transition-metal-free cascade reaction has been developed for the facile synthesis of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one derivatives from commercially available isatins and 2-haloaryl isothiocyanates. A preliminary mechanistic study suggested an interrupted Dimroth rearrangement was the key step for the successful transformation.

I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

Co-reporter:Xia Wu;Xiao Geng;Peng Zhao;Jingjing Zhang;Yan-dong Wu

Chemical Communications 2017 vol. 53(Issue 24) pp:3438-3441

Publication Date(Web):2017/03/21

DOI:10.1039/C6CC10275A

An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the CN cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

Substrates as Electron-Donor Precursors: Synthesis of Naphtho-Fused Oxindoles via Benzannulation of 2-Halobenzaldehydes and Indolin-2-ones

Co-reporter:Feng-Cheng Jia, Cheng Xu, Zhi-Wen Zhou, Qun Cai, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 20) pp:5232-5235

Publication Date(Web):October 4, 2016

DOI:10.1021/acs.orglett.6b02515

An unusual benzannulation reaction has been realized by integrating intermolecular adol condensation with subsequent intramolercular base-promoted homolytic aromatic substitution. This novel cascade reaction provides a straightforward approach toward various naphtho-fused oxindoles from 2-halobenzaldehydes and indolin-2-ones in the presence of Cs2CO3 in DMSO. The enolates of indolin-2-ones as new and internal electron donors have been demonstrated to initiate intramolecular radical dehalogenative coupling.

Direct Construction of 4-Hydroxybenzils via Para-Selective C–C Bond Coupling of Phenols and Aryl Methyl Ketones

Co-reporter:Jia-Chen Xiang, Yan Cheng, Miao Wang, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 17) pp:4360-4363

Publication Date(Web):August 11, 2016

DOI:10.1021/acs.orglett.6b02118

A highly para-selective C–C bond coupling is presented between phenols C(sp2) and aryl methyl ketones C(sp3), which enables the direct construction of 4-hydroxybenzil derivatives. This practical method exhibits a broad substrate scope and large-scale applicability and represents a general gateway to the hydroxybenzil natural product family. Mechanistic investigations indicated that the combination of HI with DMSO realized the oxidative carbonylation of aryl methyl ketones, while boric acid acted as a dual-functional relay reagent to promote this transformation.

Acid-Mediated N–H/α,β-C(sp3)–H Trifunctionalization of Pyrrolidine: Intermolecular [3 + 2] Cycloaddition for the Construction of 2,3-Dihydro-1H-Pyrrolizine Derivatives

Co-reporter:Kai-Lu Zheng, Wen-Ming Shu, Jun-Rui Ma, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 15) pp:3526-3529

Publication Date(Web):July 11, 2016

DOI:10.1021/acs.orglett.6b01369

A one-pot acid-mediated reaction has been developed for the N–H/α,β-C(sp3)–H trifunctionalization of pyrrolidine without any metallic reagents or external oxidants. This reaction involves the intermolecular [3 + 2] cycloaddition of in situ-generated azomethine ylides with acrylic esters to provide facile access to 2,3-dihydro-1H-pyrrolizine derivatives in high yields under mild conditions.

Transition-Metal-Free Coupling Annulation of Arynes with Ketones and Alkynoates: Assembly of Functionalized Naphthalenes

Co-reporter:Wen-Ming Shu, Kai-Lu Zheng, Jun-Rui Ma, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 15) pp:3762-3765

Publication Date(Web):July 27, 2016

DOI:10.1021/acs.orglett.6b01782

A transition-metal-free coupling annulation reaction of arynes, ketones, and alkynoates has been demonstrated. Using this formal [2 + 2 + 2] cycloaddition reaction, a wide variety of naphthalene derivatives were conveniently constructed in one pot with high efficiency. In addition, this novel and valid annulation has been successfully applied to the synthesis of 1-phenanthrenol derivatives.

Acid-Catalyzed Multicomponent Tandem Cyclizations: Access to Polyfunctional Dihydroindolizino[8,7-b]indoles

Co-reporter:Qun Cai, Deng-Kui Li, Rong-Rong Zhou, Wen-Ming Shu, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 6) pp:1342-1345

Publication Date(Web):February 29, 2016

DOI:10.1021/acs.orglett.6b00281

An acid-catalyzed multicomponent tandem cyclization protocol has been developed for the synthesis of polyfunctional dihydroindolizino[8,7-b]indoles from simple and readily available arylglyoxal monohydrates, tryptamines, and trans-β-nitrostyrenes or malononitrile. This reaction represents a highly efficient and convenient methodology for the synthesis of diversely substituted heteropolycyclic scaffolds under mild, metal-free conditions.

Divergent Synthesis of Quinazolin-4(3H)-ones and Tryptanthrins Enabled by a tert-Butyl Hydroperoxide/K3PO4-Promoted Oxidative Cyclization of Isatins at Room Temperature

Co-reporter:Feng-Cheng Jia, Zhi-Wen Zhou, Cheng Xu, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 12) pp:2942-2945

Publication Date(Web):May 26, 2016

DOI:10.1021/acs.orglett.6b01291

A synergetic tert-butyl hydroperoxide/K3PO4-promoted oxidative cyclization has been developed for the facile synthesis of various functionalized quinazolin-4(3H)-ones from commercially available isatins and amidine hydrochlorides at room temperature. The synthetic utility of this strategy was illustrated by the convenient synthesis of tryptanthrin derivatives via a self-dimerization of isatins under the same conditions.

Iodine-Promoted Oxidative Cross-Coupling of Unprotected Anilines with Methyl Ketones: A Site-Selective Direct C–H Bond Functionalization to C4-Dicarbonylation of Anilines

Co-reporter:Xia Wu, Qinghe Gao, Xiao Geng, Jingjing Zhang, Yan-dong Wu, and An-xin Wu

Organic Letters 2016 Volume 18(Issue 10) pp:2507-2510

Publication Date(Web):May 11, 2016

DOI:10.1021/acs.orglett.6b01162

An unprecedented direct dual C–H bond functionalization of unprotected anilines and methyl ketones has been demonstrated. It is the first example of iodine-promoted highly chemo- and site-selective oxidative C–H/C–H cross-coupling of anilines and methyl ketones to furnish the C4-dicarbonylation of anilines in moderate to good yields. Moreover, coproduct HI acted as a catalyst in the reaction. The salient feature of this approach is unprecedented C–H functionalization rather than N–H functionalization of unprotected anilines.

Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles

Co-reporter:Jingjing Zhang, Qinghe Gao, Xia Wu, Xiao Geng, Yan-Dong Wu, and Anxin Wu

Organic Letters 2016 Volume 18(Issue 7) pp:1686-1689

Publication Date(Web):March 17, 2016

DOI:10.1021/acs.orglett.6b00607

A highly efficient molecular iodine mediated Radziszewski-type reaction of methyl ketones, anilines, and tosylmethyl isocyanide has been developed. This protocol represents an elegant molecular fragment assembly of imidazoles via a formal [2 + 1 + 1 + 1] annulation. It is the first example where methyl ketones serve as the α-dicarbonyl compounds and aldehydes in Radziszewski-type reactions.

Synthesis of 2,4,5-Trisubstituted Furans via a Triple C(sp3)–H Functionalization Reaction Using Rongalite as the C1 Unit

Co-reporter:Miao Wang, Jia-Chen Xiang, Yan Cheng, Yan-Dong Wu, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 3) pp:524-527

Publication Date(Web):January 27, 2016

DOI:10.1021/acs.orglett.5b03552

A highly efficient I2/Cu(NO3)2·3H2O-mediated triple C(sp3)–H functionalization reaction for the synthesis of 2,4,5-trisubstituted furans from aryl methyl ketones and rongalite by employing rongalite as a C1 unit has been developed. This method allows rapid access to (2-acyl-4-methylthio-5-aryl) furans. Preliminary mechanistic studies indicate that in situ generated dimethyl(phenacyl)-sulfonium iodine and HCHO were probably the key intermediates in this transformation.

Multicomponent Coupling Cyclization Access to Cinnolines via in Situ Generated Diazene with Arynes, and α-Bromo Ketones

Co-reporter:Wen-Ming Shu; Jun-Rui Ma; Kai-Lu Zheng

Organic Letters 2016 Volume 18(Issue 2) pp:196-199

Publication Date(Web):December 23, 2015

DOI:10.1021/acs.orglett.5b03236

A transition-metal-free multicomponent coupling cyclization reaction was explored involving arynes, tosylhydrazine, and α-bromo ketones. The reaction proceeds via a formal [2 + 2 + 2] cycloaddition, giving access to cinnoline derivatives in moderate yields under mild conditions. Three chemical bonds were formed—two C–N bonds and one C–C bond—in a single step.

Molecular Iodine-Mediated Chemoselective Synthesis of Multisubstituted Pyridines through Catabolism and Reconstruction Behavior of Natural Amino Acids

Co-reporter:Jia-Chen Xiang, Miao Wang, Yan Cheng, and An-Xin Wu

Organic Letters 2016 Volume 18(Issue 1) pp:24-27

Publication Date(Web):December 14, 2015

DOI:10.1021/acs.orglett.5b03037

A new process has been developed for the selective construction of 2,6-disubstituted, 2,4,6-trisubstituted, and 3,5-disubstituted pyridines based on the catabolism and reconstruction behaviors of amino acids. Molecular iodine was used as a tandem catalyst to trigger the decarboxylation–deamination of amino acids and to promote the subsequent formation of the pyridine products.

An Efficient Synthesis of Polysubstituted Pyridines via Csp3H Oxidation and CS Cleavage of Dimethyl Sulfoxide

Co-reporter:Xia Wu;Jingjing Zhang;Shan Liu;Qinghe Gao;Anxin Wu

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 2) pp:218-225

Publication Date(Web):

DOI:10.1002/adsc.201500683

Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromoaldehydes, Benzylamines, and Sodium Azide for the Assembly of Quinazoline Derivatives

Co-reporter:Cheng Xu, Feng-Cheng Jia, Zhi-Wen Zhou, Si-Jie Zheng, Han Li, and An-Xin Wu

The Journal of Organic Chemistry 2016 Volume 81(Issue 7) pp:3000-3006

Publication Date(Web):March 9, 2016

DOI:10.1021/acs.joc.5b02843

An efficient three-component domino reaction of 2-bromoaldehydes, benzylamines, and sodium azide has been developed for the synthesis of quinazoline derivatives. This domino process involves copper-catalyzed SNAr, oxidation/cyclization, and denitrogenation sequences. The mild catalytic system enabled the effective construction of three C–N bonds in one operation.

Base-promoted domino reaction for the synthesis of 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes

Co-reporter:Yan-Dong Wu, Jun-Rui Ma, Wen-Ming Shu, Kai-Lu Zheng, An-Xin Wu

Tetrahedron 2016 Volume 72(Issue 32) pp:4821-4826

Publication Date(Web):11 August 2016

DOI:10.1016/j.tet.2016.06.046

A base-promoted domino reaction to synthesize the 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes has been developed. This strategy provides a simple and beneficial way for the construction of 2,3-disubstituted indole compounds from readily available starting materials under mild conditions.

Acid-Catalyzed Multicomponent Tandem Double Cyclization: A One-pot, Metal-free Route to Synthesize Polyfunctional 4,9-Dihydropyrrolo[2,1-b]quinazolines

Co-reporter:Qun Cai, Deng-Kui Li, Rong-Rong Zhou, Shi-Yi Zhuang, Jin-Tian Ma, Yan-Dong Wu, and An-Xin Wu

The Journal of Organic Chemistry 2016 Volume 81(Issue 17) pp:8104-8111

Publication Date(Web):August 9, 2016

DOI:10.1021/acs.joc.6b01660

An acid-catalyzed multicomponent tandem double cyclization protocol has been developed for the synthesis of polyfunctional 4,9-dihydropyrrolo[2,1-b]quinazolines from simple and readily available arylglyoxal monohydrates, 2-aminobenzylamine, and trans-β-nitrostyrenes. This practical and metal-free reaction proceeds through an imine formation/cyclization/Michael addition/Henry cyclization protocol, resulting in the construction of four new bonds and two ring moieties directly in one pot.

Intramolecular decarboxylative coupling as the key step in copper-catalyzed domino reaction: facile access to 2-(1,3,4-oxadiazol-2-yl)aniline derivatives

Co-reporter:Cheng Xu, Feng-Cheng Jia, Qun Cai, Deng-Kui Li, Zhi-Wen Zhou and An-Xin Wu

Chemical Communications 2015 vol. 51(Issue 30) pp:6629-6632

Publication Date(Web):05 Mar 2015

DOI:10.1039/C5CC01116G

A copper-catalyzed domino protocol for the synthesis of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives has been developed from simple and available isatins and hydrazides. This domino process integrated consecutive condensation, base-promoted ring-opening and the key copper-catalyzed decarboxylative coupling for intramolecular C–O bond formation.

Transition-Metal-Free Multicomponent Benzannulation Reactions for the Construction of Polysubstituted Benzene Derivatives

Co-reporter:Wen-Ming Shu, Kai-Lu Zheng, Jun-Rui Ma, and An-Xin Wu

Organic Letters 2015 Volume 17(Issue 21) pp:5216-5219

Publication Date(Web):October 16, 2015

DOI:10.1021/acs.orglett.5b02548

A transition-metal-free multicomponent benzannulation reaction was developed from readily available ketones, nitro-olefins, and diester acetylenedicarboxylate. This approach provides a straightforward and efficient way to construct polysubstituted benzene derivatives under mild conditions in high yields.

Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy

Co-reporter:Feng-Cheng Jia, Zhi-Wen Zhou, Cheng Xu, Qun Cai, Deng-Kui Li, and An-Xin Wu

Organic Letters 2015 Volume 17(Issue 17) pp:4236-4239

Publication Date(Web):August 24, 2015

DOI:10.1021/acs.orglett.5b02020

A highly efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved consecutive iron-mediated [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, oxidation, and copper-catalyzed denitrogenation sequences. The formed structure is the privileged core in drugs and bioactive molecules.

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)–C(Methyl) Bond Cleavage of Methyl Ketones

Co-reporter:Qinghe Gao, Shan Liu, Xia Wu, Jingjing Zhang, and Anxin Wu

Organic Letters 2015 Volume 17(Issue 12) pp:2960-2963

Publication Date(Web):June 2, 2015

DOI:10.1021/acs.orglett.5b01241

A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C–C bond cleavage. This reaction is proposed to go through oxidative cleavage of Csp3–H bonds, followed by cyclization and deacylation.

Consecutive Cycloaddition/SNAr/Reduction/Cyclization/Oxidation Sequences: A Copper-Catalyzed Multicomponent Synthesis of Fused N-Heterocycles

Co-reporter:Feng-Cheng Jia, Cheng Xu, Zhi-Wen Zhou, Qun Cai, Deng-Kui Li, and An-Xin Wu

Organic Letters 2015 Volume 17(Issue 11) pp:2820-2823

Publication Date(Web):May 21, 2015

DOI:10.1021/acs.orglett.5b01242

A highly efficient multicomponent domino protocol has been developed for the synthesis of 5-phenyl-[1,2,3]triazolo[1,5-c]quinazolines from simple and readily available (E)-1-bromo-2-(2-nitrovinyl)benzenes, aldehydes, and sodium azide. This elegant domino process involved consecutive [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, and oxidation sequences. Notably, sodium azide acted as a dual nitrogen source in the construction of this novel fused N-heterocycle.

Convenient Access to Polyfunctional Pyrazoles via a Highly Efficient and Regioselective Multicomponent Reaction

Co-reporter:Wen-Ming Shu, Kai-Lu Zheng, Jun-Rui Ma, Hui-Ying Sun, Mei Wang, and An-Xin Wu

Organic Letters 2015 Volume 17(Issue 8) pp:1914-1917

Publication Date(Web):March 31, 2015

DOI:10.1021/acs.orglett.5b00605

A multicomponent reaction has been developed for the synthesis of polyfunctional pyrazole derivatives from readily available arylglyoxal monohydrates, tosylhydrazine, and aldehydes or ketones. This synthetic method has significant advantages in broad substrate scope, excellent regioselectivity, and simple operation.

Direct Regioselective Oxidative Cross-Coupling of Indoles with Methyl Ketones: A Novel Route to C3-Dicarbonylation of Indoles

Co-reporter:Qinghe Gao, Jingjing Zhang, Xia Wu, Shan Liu, and Anxin Wu

Organic Letters 2015 Volume 17(Issue 1) pp:134-137

Publication Date(Web):December 15, 2014

DOI:10.1021/ol503366r

The first C3-dicarbonylation of indoles was realized through direct oxidative cross-coupling of indoles with methyl ketones in the presence of molecular iodine and pyrrolidine. This reaction constructed a highly efficient indolyl diketones scaffold, which might be regarded as a useful biological and pharmacological tool in the exploration of therapeutic A2BAR modulators. The use of inexpensive molecular iodine and pyrrolidine and a broad substrate scope make this protocol very practical. Preliminary mechanistic studies indicate that two paths are involved in this process.

Formamidine hydrochloride as an amino surrogate: I2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N–H) α-ketoamides

Co-reporter:Shan Liu, Qinghe Gao, Xia Wu, Jingjing Zhang, Kerong Ding and Anxin Wu

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 8) pp:2239-2242

Publication Date(Web):05 Jan 2015

DOI:10.1039/C4OB02591A

A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones with formamidine hydrochloride has been developed. This reaction represents a novel strategy for the synthesis of free (N–H) α-ketoamides. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/amidation/oxidation/decarbonylation mechanism was proposed.

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles

Co-reporter:Jiachen Xiang, Jungang Wang, Miao Wang, Xianggao Meng and Anxin Wu

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 14) pp:4240-4247

Publication Date(Web):25 Feb 2015

DOI:10.1039/C5OB00025D

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones.

Efficient approach to 2-hydroxy-2,3-dihydrofuran derivatives and its application for the synthesis of novel 4-(1H-pyrazol-4-yl)pyridazines

Co-reporter:Jun-Rui Ma, Wen-Ming Shu, Kai-Lu Zheng, Fan Ni, Guo-Dong Yin and An-Xin Wu

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 17) pp:4976-4980

Publication Date(Web):30 Mar 2015

DOI:10.1039/C5OB00163C

A highly efficient method for the synthesis of 2-hydroxy-2,3-dihydrofuran derivatives from 1,4-enediones and phenacyl pyridinium halides via a domino reaction has been developed. This is a simple and beneficial strategy for the construction of 2-hydroxy-2,3-dihydrofuran compounds from readily available starting materials under mild conditions. Moreover, the application of this reaction provides a straightforward and practical route for the synthesis of the novel 4-(1H-pyrazol-4-yl)pyridazine skeleton.

Organopromoted direct synthesis of 6-iodo-3-methylthioimidazo[1,2-a]pyridines via convergent integration of three self-sorting domino sequences

Co-reporter:Shan Liu, Hailing Xi, Jingjing Zhang, Xia Wu, Qinghe Gao and Anxin Wu

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 33) pp:8807-8811

Publication Date(Web):17 Jul 2015

DOI:10.1039/C5OB01313E

An NH2CN-promoted convergent integration of three self-sorting domino sequences is described for the construction of 6-iodo-3-methylthioimidazo[1,2-a]pyridines from aryl methyl ketones and 2-aminopyridines. This strategy allows the construction of an imidazo[1,2-a]pyridine ring along with methylthiolation at C-3 and iodination at C-6. Preliminary mechanistic studies indicate that this process terminates at the iodination stage without Kornblum oxidation in the presence of I2 and DMSO.

X-ray studies of conformation: observation of conformational polymorphism of a glycoluril clip

Co-reporter:Jungang Wang, Yang Gao, Jiachen Xiang, Miao Wang and Anxin Wu

CrystEngComm 2015 vol. 17(Issue 11) pp:2245-2249

Publication Date(Web):04 Feb 2015

DOI:10.1039/C5CE00066A

In order to study the conformational behavior of a glycoluril clip, compound 1 was synthesized and X-ray crystallography, NMR spectroscopy, and molecular modeling were used in the work. The results of the computational studies revealed the stability of the four conformers retained the order aa > as ≈ sa > ss in both gas and solvation models, while solvation decreased the relative energies of each conformer dramatically. In the solid phase, X-ray crystallographic analysis indicated that compound 1 presented conformational polymorphism when it crystallized in various solvents. We fortunately obtained a single crystal of the aa and as conformers of the same glycoluril clip. The X-ray crystallographic analysis in this report provides the first crystallographic evidence of the conformers of a glycoluril clip. Unlike in the solid state, the conformers interconvert rapidly in solution and therefore cannot be detected on the NMR timescale.

CuO/I2-mediated intramolecular annulation for the synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes

Co-reporter:Qun Cai, Yan Yang, Deng-Kui Li, Feng-Cheng Jia, Cheng Xu and An-Xin Wu

RSC Advances 2015 vol. 5(Issue 109) pp:89427-89430

Publication Date(Web):13 Oct 2015

DOI:10.1039/C5RA17651D

A novel strategy has been developed for the direct synthesis of 2-aroyl-3-hydroxy-4-iodonaphthalenes from easily available (Z)-2-(hetero)arylidene-1-(hetero)arylbutane-1,3-diones in the presence of copper(II) oxide and iodine. This domino process involves consecutive methyl iodination/carbon–carbon double bond isomerization/6π-electrocyclization/aromatization/arene iodination sequences.

A Regioselective Formal Coupling Reaction Between C(sp2) and C(sp3): o-Quinodimethane (o-QDM)-Mediated Domino Process for the Construction of 3-(2-methylbenzyl)indole Derivatives

Co-reporter:Miao Wang;Jungang Wang;Jiachen Xiang ;Anxin Wu

Asian Journal of Organic Chemistry 2015 Volume 4( Issue 8) pp:741-744

Publication Date(Web):

DOI:10.1002/ajoc.201500123

Abstract

In this work, a metal-free, regioselective, formal coupling reaction between C(sp²) of indoles and the C(sp³) of benzo[c]oxepines has been realized. This method provides an efficient approach for the synthesis of 3-(2-methylbenzyl)indole derivatives. Based on the experimental results, a sequential ring-opening/[1,5]H-shift/Michael addition mechanism was proposed.

Molecular iodine mediated oxidative cross-coupling of sp3 C–H with sp2 C–H: direct synthesis of substituted indolo[2,3-b]carbazoles via formal [2+2+1+1] cyclization

Co-reporter:Wei-jian Xue, Qing-He Gao, An-xin Wu

Tetrahedron Letters 2015 Volume 56(Issue 51) pp:7115-7119

Publication Date(Web):23 December 2015

DOI:10.1016/j.tetlet.2015.11.026

A molecular iodine mediated oxidative cross-coupling of β-keto ester sp3 C–H with 1H-indole sp2 C–H was developed for the synthesis of indolo[2,3-b]carbazoles. A self-sequenced iodination/Kornblum oxidation/hydrolyzation/decarboxylative/deacylation/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study.

A multipathway coupled domino strategy: I2-mediated oxidative thionation for direct synthesis of thiobenzamides from miscellaneous substrates

Co-reporter:Hong-Zheng Li, Wei-Jian Xue, Guo-Dong Yin, An-Xin Wu

Tetrahedron Letters 2015 Volume 56(Issue 43) pp:5843-5846

Publication Date(Web):21 October 2015

DOI:10.1016/j.tetlet.2015.08.060

An efficient iodine-mediated multipathway coupled domino reaction has been developed for the synthesis of thiobenzamides from benzylamines, benzylamines/aldehydes, and N-alkyl benzylamines under the same reaction conditions. This approach combines two consecutive domino processes in one pot using iodine as the oxidant.

Coproduct Promoted Povarov Reaction: Synthesis of Substituted Quinolines from Methyl Ketones, Arylamines, and α-Ketoesters

Co-reporter:Qinghe Gao, Shan Liu, Xia Wu, Jingjing Zhang, and Anxin Wu

The Journal of Organic Chemistry 2015 Volume 80(Issue 11) pp:5984-5991

Publication Date(Web):May 14, 2015

DOI:10.1021/acs.joc.5b00785

A highly efficient I2-catalyzed Povarov-type reaction of methyl ketones, arylamines, and α-ketoesters is developed. This reaction utilizes a catalytic amount of HI coproduct as a promoter for the synthesis of substituted quinolones. This simple procedure represents an interesting new form of reactivity for the Povarov reaction with good functional group compatibility.

Generation of o-quinodimethanes (o-QDMs) from benzo[c]oxepines and the synthetic application for polysubstituted tetrahydronaphthalenes

Co-reporter:Jungang Wang, Miao Wang, Jiachen Xiang, Hailing Xi, Anxin Wu

Tetrahedron 2015 Volume 71(Issue 40) pp:7687-7694

Publication Date(Web):7 October 2015

DOI:10.1016/j.tet.2015.07.062

A novel method for the generation of o-quinodimethane (o-QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[c]oxepines. Among the benzo[c]oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o-QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o-QDM intermediates from benzo[c]oxepine precursors.

Chemoselective synthesis of biheterocyclic skeletons tetrahydro-1H-pyrrolo[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives via multicomponent self-sorting domino strategy

Co-reporter:Qun Cai, Feng-Cheng Jia, Deng-Kui Li, Cheng Xu, Ke-Rong Ding, An-Xin Wu

Tetrahedron 2015 Volume 71(Issue 36) pp:6104-6111

Publication Date(Web):9 September 2015

DOI:10.1016/j.tet.2015.06.104

A highly efficient chemoselective synthesis of multifunctionalized tetrahydro-1H-pyrrolo[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives has been established from arylglyoxal monohydrates, nitriles, and thioureas. A series of control experiments suggested that this reaction proceeded through the convergent integration of two self-sorting domino sequences. This synthetic strategy is promising for diversity-oriented synthesis of alkaloid analogues.

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones

Co-reporter:Feng-Cheng Jia, Cheng Xu, Qun Cai and An-Xin Wu

Chemical Communications 2014 vol. 50(Issue 69) pp:9914-9916

Publication Date(Web):27 Jun 2014

DOI:10.1039/C4CC03420A

A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermolecular C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction.

Povarov-Type Reaction Using Methyl as New Input: Direct Synthesis of Substituted Quinolines by I2-Mediated Formal [3 + 2 + 1] Cycloaddition

Co-reporter:Qinghe Gao, Shan Liu, Xia Wu, and Anxin Wu

Organic Letters 2014 Volume 16(Issue 17) pp:4582-4585

Publication Date(Web):August 13, 2014

DOI:10.1021/ol502134u

A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction for the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes is developed. The methyl group of the methyl ketone represents uniquely reactive input in the Povarov reaction. A self-sequenced iodination/Kornblum oxidation/Povarov/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study.

I2-Catalyzed Oxidative Cross-Coupling of Methyl Ketones and Benzamidines Hydrochloride: A Facile Access to α-Ketoimides

Co-reporter:Xia Wu, Qinghe Gao, Shan Liu, and Anxin Wu

Organic Letters 2014 Volume 16(Issue 11) pp:2888-2891

Publication Date(Web):May 15, 2014

DOI:10.1021/ol501029w

An iodine-catalyzed oxidative cross-coupling of C–H/N–H has been demonstrated. This simple and efficient approach constructed α-ketoimides in good to excellent yields from methyl ketones and benzamidines hydrochloride under metal-free and peroxide-free conditions. This synthetic strategy was achieved via an in situ iodination-based oxidative coupling pathway.

I2-Promoted Selective Oxidative Cross-Coupling/Annulation of 2-Naphthols with Methyl Ketones: A Strategy To Build Naphtho[2,1-b]furan-1(2H)-ones with a Quaternary Center

Co-reporter:Qinghe Gao, Xia Wu, Shan Liu, and Anxin Wu

Organic Letters 2014 Volume 16(Issue 6) pp:1732-1735

Publication Date(Web):March 3, 2014

DOI:10.1021/ol5004093

A highly efficient and selective molecular iodine-promoted oxidative cross-coupling/annulation between 2-naphthols and methyl ketones has been realized. The reaction successfully constructed a new quaternary carbon center within 3(2H)-furanones. Our synthetic strategy provided an in situ iodination-based oxidative coupling pathway. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/Friedel–Crafts/oxidation/cyclization mechanism was proposed.

An Efficient Synthesis of Novel Fused Cycloheptatrienes through Mn(II)-Mediated Formal Intermolecular [2 + 2 + 2 + 1] Cycloaddition

Co-reporter:Wen-Ming Shu, Jun-Rui Ma, Yan Yang, and An-Xin Wu

Organic Letters 2014 Volume 16(Issue 5) pp:1286-1289

Publication Date(Web):February 24, 2014

DOI:10.1021/ol500202q

A new method for manganous acetate tetrahydrate mediated formal intermolecular [2 + 2 + 2 + 1] cycloaddition was developed for the synthesis of fused cycloheptatriene derivatives from N-(acylmethyl)pyridinium iodides and naphthoquinone. This method provides an innovative route for the efficient and convenient construction of fused seven-membered carbocycles from simple starting materials.

Iodine-Promoted Sequential C(sp3)H Functionalization Reactions: An Annulation Strategy for the Construction of 3-Methylthio-4-arylmaleimides

Co-reporter:Qinghe Gao;Xia Wu;Yuhong Li;Shan Liu;Xianggao Meng ;Anxin Wu

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 14-15) pp:2924-2930

Publication Date(Web):

DOI:10.1002/adsc.201400474

Brønsted acid promoted addition–cyclization and C–C bond cleavage: a convenient synthesis of 2-amino-5-aroylmethylthiazoles derivatives

Co-reporter:Fan Ni, Yan Yang, Wen-Ming Shu, Jun-Rui Ma and An-Xin Wu

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 46) pp:9466-9470

Publication Date(Web):20 Oct 2014

DOI:10.1039/C4OB01519C

A Brønsted acid promoted C–C bond cleavage method for the synthesis of novel 2-amino-5-aroylmethylthiazole derivatives has been directly developed from 1,4-enediones and thioureas through self-sequenced thio-Michael-addition, intramolecular selective cyclization, dehydration/aromatization, and C–C bond cleavage reactions. It is noteworthy that this reaction has significant advantages in simple reagents, under environmentally benign conditions and with excellent yields. This highly efficient method is also a highly attractive alternative for the preparation of PLTP, CETP inhibitors and novel biheterocycles.

Direct synthesis of α-hydroxyacetophenones through molecular iodine activation of carbon–carbon double bonds

Co-reporter:Xia Wu, Qinghe Gao, Mi Lian, Shan Liu and Anxin Wu

RSC Advances 2014 vol. 4(Issue 93) pp:51180-51183

Publication Date(Web):07 Oct 2014

DOI:10.1039/C4RA07012G

An I2-promoted activation of carbon–carbon double bonds has been demonstrated. This simple and efficient domino process was utilized for the direct construction of α-hydroxyacetophenones in moderate to good yields from easily available styrenes at room temperature. This approach involved molecular iodine activation of carbon–carbon double bonds to form an iodonium intermediate. Moreover, TBHP was used as the sole effective oxidant and water was used as nucleophilic reagent in this reaction.

Convergent integration of three self-sorting domino sequences: three-component direct synthesis of 3-methylthio-4-aryl-maleimides from methyl ketones with acetonitrile and DMSO

Co-reporter:Qinghe Gao, Shan Liu, Xia Wu, Anxin Wu

Tetrahedron Letters 2014 Volume 55(Issue 47) pp:6403-6406

Publication Date(Web):19 November 2014

DOI:10.1016/j.tetlet.2014.09.099

An I2-promoted three-component coupling reaction was described for the construction of 3-(methylthio)-4-aryl-1H-pyrrole-2,5-diones from methyl ketones with acetonitrile and DMSO. This transformation involved the in situ generation and application of α-ketoimides. Furthermore, DMSO was converted to DMS in situ, which subsequently served as a methylthiolation reagent in the reaction. To the best of our knowledge, this protocol provided the first known example of convergent integration of three self-sorting domino sequences.

Iodine-promoted efficient synthesis of diheteroaryl thioethers via the integration of iodination/condensation/cyclization/dehydration sequences

Co-reporter:Wei-jian Xue, Hong-zheng Li, Kai-lu Zheng, An-xin Wu

Tetrahedron Letters 2014 Volume 55(Issue 40) pp:5544-5547

Publication Date(Web):1 October 2014

DOI:10.1016/j.tetlet.2014.08.042

A novel method for the construction of diheteroaryl thioethers from aromatic methyl ketones and thiourea is described. Iodine is the unique catalyst in this protocol. The transformation is free of foul-smell thiols and transition metal. In addition, this method could synthesize two thiazole rings and a sulfur bridge in one pot.

Iodine-promoted selective synthesis of substituted aminothiazole via a self-sorting reaction network

Co-reporter:Wei-jian Xue, Kai-lu Zheng, Hong-zheng Li, Fang-fang Gao, An-xin Wu

Tetrahedron Letters 2014 Volume 55(Issue 30) pp:4212-4215

Publication Date(Web):23 July 2014

DOI:10.1016/j.tetlet.2014.05.101

An iodine-promoted selective synthesis has been developed for the construction of substituted aminothiazole from easily available aryl methyl ketones and thiourea under metal free conditions. This domino process involves the cleavage of CH, CO, CS bonds and the formation of CN, CO, CS bonds.

One-pot total synthesis: the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids

Co-reporter:Jiachen Xiang, Jungang Wang, Miao Wang, Xianggao Meng, Anxin Wu

Tetrahedron 2014 70(41) pp: 7470-7475

Publication Date(Web):

DOI:10.1016/j.tet.2014.08.022

Synthesis of substituted naphthalenes from α-substituted ketones and 1,2-bis(halomethyl)benzenes including a rearrangement aromatization of benzo[c]oxepine

Co-reporter:Jungang Wang, Jiachen Xiang, Miao Wang, Jie Guan, Anxin Wu

Tetrahedron 2014 70(7) pp: 1412-1417

Publication Date(Web):

DOI:10.1016/j.tet.2014.01.005

Logical design and synthesis of indole-2,3-diones and 2-hydroxy-3(2H)-benzofuranones via one-pot intramolecular cyclization

Co-reporter:Fang-Fang Gao, Wei-Jian Xue, Jun-Gang Wang, An-Xin Wu

Tetrahedron 2014 70(29) pp: 4331-4335

Publication Date(Web):

DOI:10.1016/j.tet.2014.05.015

Synthesis of trisubstituted imidazoles via a convergent reaction network from methyl ketones and benzoins

Co-reporter:Wei-Jian Xue, Hong-Zheng Li, Fang-Fang Gao, Anxin Wu

Tetrahedron 2014 70(2) pp: 239-244

Publication Date(Web):

DOI:10.1016/j.tet.2013.11.080

Electronic tuning cyclization of aryl-1,4-enediones: AlCl3-mediated Nazarov-type cyclization to synthesize polysubstituted-1-indanones

Co-reporter:Yan-Ping Zhu, Qun Cai, Feng-Cheng Jia, Mei-Cai Liu, Qing-He Gao, Xiang-Gao Meng, An-Xin Wu

Tetrahedron 2014 70(50) pp: 9536-9544

Publication Date(Web):

DOI:10.1016/j.tet.2014.10.052

One-pot synthesis of polyfunctional pyrazoles: an easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

Co-reporter:Wen-Ming Shu, Jun-Rui Ma, Kai-Lu Zheng, Hui-Ying Sun, Mei Wang, Yan Yang, An-Xin Wu

Tetrahedron 2014 70(49) pp: 9321-9329

Publication Date(Web):

DOI:10.1016/j.tet.2014.10.044

Water as an additive for selective synthesis of saturated 1,4-diketones and tetrasubstituted furans directly from 1,4-enediones

Co-reporter:Yan Yang, Fan Ni, Wen-Ming Shu, An-Xin Wu

Tetrahedron 2014 70(38) pp: 6733-6741

Publication Date(Web):

DOI:10.1016/j.tet.2014.07.077

Direct synthesis of α-ketothioamides from aryl methyl ketones and amines via I2-promoted sp3 C–H functionalization

Co-reporter:Hong-Zheng Li, Wei-Jian Xue, An-Xin Wu

Tetrahedron 2014 70(31) pp: 4645-4651

Publication Date(Web):

DOI:10.1016/j.tet.2014.05.045

Copper-Catalyzed Domino Synthesis of 2-Imino-1H-imidazol-5(2H)-ones and Quinoxalines Involving CC Bond Cleavage with a 1,3-Dicarbonyl Unit as a Leaving Group

Co-reporter:Yan Yang;Fan Ni;Wen-Ming Shu; An-Xin Wu

Chemistry - A European Journal 2014 Volume 20( Issue 37) pp:11776-11782

Publication Date(Web):

DOI:10.1002/chem.201403001

Abstract

Although 2-imino-1H-imidazol-5(2H)-ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as “privileged scaffolds” in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper-catalyzed domino reactions for the synthesis of 2-imino-1H-imidazol-5(2H)-ones and quinoxalines involving CC bond-cleavage with a 1,3-dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2-imino-1H-imidazol-5(2H)-ones includes aza-Michael addition, intramolecular cyclization, CC bond-cleavage, 1,2-rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza-Michael addition, intramolecular cyclization, elimination reaction, and CC bond-cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups.

A Novel Self-Sequence Reaction Network Involving a Set of Six Reactions in One Pot: The Synthesis of Substituted Benzothiazoles from Aromatic Ketones and Anilines

Co-reporter:Wei-Jian Xue, Ya-Qiong Guo, Fang-Fang Gao, Hong-Zheng Li, and An-Xin Wu

Organic Letters 2013 Volume 15(Issue 4) pp:890-893

Publication Date(Web):January 31, 2013

DOI:10.1021/ol400029t

Employing simple and readily available aromatic ketones and anilines as starting materials resulted in the construction of 2-acylbenzothiazoles via a novel self-sequence reaction network, which assembles six reactions in one pot. The reaction network not only supplied a novel method for constructing complex molecules but also provided a typical example for logical self-organization synthesis.

Highly Efficient Synthesis of 3a,6a-Dihydrofuro[2,3-b]furans via a Novel Bicyclization

Co-reporter:Wen-Ming Shu, Yan Yang, Dong-Xue Zhang, Liu-Ming Wu, Yan-Ping Zhu, Guo-Dong Yin, and An-Xin Wu

Organic Letters 2013 Volume 15(Issue 3) pp:456-459

Publication Date(Web):January 11, 2013

DOI:10.1021/ol400016c

A highly efficient method for the construction of 3a,6a-dihydrofuro[2,3-b]furan derivatives has been developed via a novel bicyclization, which is very valuable for the synthesis of fused furofuran compounds since it is time-saving and catalyst-free. Based on the bicyclization, a coupled domino strategy has been developed to directly construct 3a,6a-dihydrofuro[2,3-b]furan derivatives from methyl ketones.

Direct One-Pot Synthesis of Luotonin F and Analogues via Rational Logical Design

Co-reporter:Yan-ping Zhu, Zhuan Fei, Mei-cai Liu, Feng-cheng Jia, and An-xin Wu

Organic Letters 2013 Volume 15(Issue 2) pp:378-381

Publication Date(Web):December 28, 2012

DOI:10.1021/ol303331g

An efficient one-pot synthetic protocol has been proposed for the synthesis of luntonin F from easily available starting materials. Through a rational logical design, multifundamental reactions (iodination, Kornblum oxidation, and annulation) were assembled in one-pot. The developed approach can efficiently synthesize luntonin F and a diversity of analogues.

Auto-tandem catalysis: synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones via copper-catalyzed aza-Michael addition–aerobic dehydrogenation–intramolecular amidation

Co-reporter:Yan Yang, Wen-Ming Shu, Shang-Bo Yu, Fan Ni, Meng Gao and An-Xin Wu

Chemical Communications 2013 vol. 49(Issue 17) pp:1729-1731

Publication Date(Web):11 Jan 2013

DOI:10.1039/C3CC38131E

A copper-catalyzed domino synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed from 1,4-enediones and 2-aminoheterocycles with air as the oxidant.

Robust R22(8) hydrogen bonded dimer for crystal engineering of glycoluril derivatives

Co-reporter:Jungang Wang, Jiachen Xiang, Anxin Wu and Xianggao Meng

CrystEngComm 2013 vol. 15(Issue 46) pp:10079-10085

Publication Date(Web):17 Sep 2013

DOI:10.1039/C3CE41702F

A series of glycoluril derivatives 1–3 were examined through crystallographic characterization to reveal a highly conserved amide⋯amide homosynthon, with intermolecular R22(8) hydrogen bonding interactions. As expected, the intermolecular hydrogen bonding interactions promoted the dimerization of the building blocks 1–3, even in the presence of competing pyridine rings and various solvent molecules. These robust dimer synthons were then connected to form a one-dimensional chain through C–H⋯O interactions and further extended to a two-dimensional layer by additional C–H⋯π interactions. This robust hydrogen bond motif was achieved without interference from competing intermolecular interactions and significant changes in the hydrocarbon core, and as such has much potential for application as a supramolecular synthon for solid-state design.

A new selective pyrazoline-based fluorescent chemosensor for Cu2+ in aqueous solution

Co-reporter:Shengli Hu, Shushu Zhang, Yang Hu, Qing Tao, Anxin Wu

Dyes and Pigments 2013 Volume 96(Issue 2) pp:509-515

Publication Date(Web):February 2013

DOI:10.1016/j.dyepig.2012.09.019

A new pyrazoline derivate was designed and synthesized. The structure of the pyrazoline was confirmed by single crystal X-ray diffraction and its photophysical properties were studied by absorption and fluorescence spectra. This compound can be used to determine Cu2+ ion with high selectivity and sensitivity among a series of cations in aqueous tetrahydrofuran. This sensor forms a 1:1 complex with Cu2+ and displays fluorescent quenching.Graphical abstractPyrazoline derivate 1 for selective detection of Cu2+ with fluorescence quenching.Highlights► The pyrazoline derived sensor is simple to synthesize. ► The structure of the pyrazoline was confirmed by single crystal X-ray diffraction. ► This sensor can be used to determine Cu2+ ion with high selectivity and a low detection limit. ► It is the first example of Cu2+ ion fluorescent chemosensor in aqueous solution based on pyrazoline chromophore.

Synthesis of α-iodoketals from methyl ketones via sustainable and orthogonal tandem catalysis

Co-reporter:Yan Yang, Meng Gao, Wen-Ming Shu, Liu-Ming Wu, Dong-Xue Zhang and An-Xin Wu

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 7) pp:1226-1233

Publication Date(Web):19 Dec 2012

DOI:10.1039/C2OB27028E

A highly efficient method for the direct synthesis of α-iodoketals from methyl ketones has been developed via sustainable integration of orthogonal tandem catalytic reactions: copper(II) oxide catalyzed iodination reaction and the subsequent excess or regenerated iodine catalyzed regioselective ketalization reaction.

A benzimidazole-based ratiometric fluorescent sensor for Cr3+ and Fe3+ in aqueous solution

Co-reporter:Meng Wang, Jungang Wang, Weijian Xue, Anxin Wu

Dyes and Pigments 2013 Volume 97(Issue 3) pp:475-480

Publication Date(Web):June 2013

DOI:10.1016/j.dyepig.2013.02.005

A novel ratiometric fluorescent sensor bearing two benzimidazole groups has been synthesized. The sensor showed a ratiometric fluorescence response with an enhancement of the ratios of emission intensities at 443 and 378 nm from 0.17 to 3.21 for Cr3+. The ratios of emission intensities at 443 and 380 nm were enhanced from 0.40 to 2.09 for Fe3+. Fe3+ revealed significant adsorption in the UV–vis region, which can be used to discriminate Cr3+ and Fe3+. Detection limits of the method for Cr3+ and Fe3+ were 25 μM and 2 μM, respectively. In addition, the sensor showed good selectivity to Cr3+ and Fe3+ over other metal ions.

Inside Cover: Formation of 2-Acyloxazoles by a Multipathway Coupled Domino Strategy: One-Pot Metal-Free Oxidative Cyclization Applicable to Various Substrates (Asian J. Org. Chem. 8/2013)

Co-reporter:Wei-Jian Xue;Wei Zhang;Kai-Lu Zheng;Yun Dai;Ya-Qiong Guo;Hong-Zheng Li;Fang-Fang Gao ; An-Xin Wu

Asian Journal of Organic Chemistry 2013 Volume 2( Issue 8) pp:

Publication Date(Web):

DOI:10.1002/ajoc.201390022

Formation of 2-Acyloxazoles by a Multipathway Coupled Domino Strategy: One-Pot Metal-Free Oxidative Cyclization Applicable to Various Substrates

Co-reporter:Wei-Jian Xue;Wei Zhang;Kai-Lu Zheng;Yun Dai;Ya-Qiong Guo;Hong-Zheng Li;Fang-Fang Gao ; An-Xin Wu

Asian Journal of Organic Chemistry 2013 Volume 2( Issue 8) pp:638-641

Publication Date(Web):

DOI:10.1002/ajoc.201300124

I2-promoted direct one-pot synthesis of 2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines from aromatic ketones and 2-aminopyridines

Co-reporter:Zhuan Fei, Yan-ping Zhu, Mei-cai Liu, Feng-cheng Jia, An-xin Wu

Tetrahedron Letters 2013 Volume 54(Issue 10) pp:1222-1226

Publication Date(Web):6 March 2013

DOI:10.1016/j.tetlet.2012.12.072

An I2-promoted one-pot protocol was proposed for the synthesis of 2-aryl-3-(pyridine-2-ylamino)imidazo[1,2-a]pyridines from aromatic ketones and 2-aminopyridines. The present reaction proceeded well in the presence of I2 in DMSO, and it avoided the requirement of any metal, base, and ligand.

I2-promoted direct one-pot synthesis of 2,2-bisindolyl-1-arylethanones from multiform substrates arylethenes, 2-hydroxy-aromatic ketones, and carbinols

Co-reporter:Feng-Cheng Jia, Yan-Ping Zhu, Mei-Cai Liu, Mi Lian, Qing-He Gao, Qun Cai, An-Xin Wu

Tetrahedron 2013 69(34) pp: 7038-7044

Publication Date(Web):

DOI:10.1016/j.tet.2013.06.054

A new route to construct 1,2-dihydroquinoxaline and 1,4-benzoxazine derivatives stereoselectively and its application to novel pyrazolo[1,5-α]quinoxaline oxides

Co-reporter:Dongxue Zhang, Yan Yang, Meng Gao, Wenming Shu, Liuming Wu, Yanping Zhu, Anxin Wu

Tetrahedron 2013 69(7) pp: 1849-1856

Publication Date(Web):

DOI:10.1016/j.tet.2012.12.060

Target-oriented synthesis: miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates

Co-reporter:Yan-ping Zhu, Qun Cai, Qing-he Gao, Feng-cheng Jia, Mei-cai Liu, Meng Gao, An-xin Wu

Tetrahedron 2013 69(31) pp: 6392-6398

Publication Date(Web):

DOI:10.1016/j.tet.2013.05.106

Synthesis of Tetrasubstituted Unsymmetrical 1,4-Enediones via Copper-Promoted Autotandem Catalysis and Air As the Oxidant

Co-reporter:Yan Yang, Fan Ni, Wen-Ming Shu, Shang-Bo Yu, Meng Gao, and An-Xin Wu

The Journal of Organic Chemistry 2013 Volume 78(Issue 11) pp:5418-5426

Publication Date(Web):May 6, 2013

DOI:10.1021/jo400564f

An efficient procedure has been developed for the preparation of tetrasubstituted unsymmetrical 1,4-enediones via copper-promoted autotandem catalysis and air as the oxidant. Various N-nucleophiles are compatible with this reaction, such as morpholine, piperidine, pyrrolidine, arylamines, pyrazole, imidazole, benzimidazole, and benzotriazole. This reaction also has significant advantages in easily available substrates, atom economy, bond-forming efficiency, and environmental benignity.

Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Michael Addition/Bicyclization Reaction

Co-reporter:Guodong Yin, Tianbing Ren, Yin Rao, Yifan Zhou, Zhexian Li, Wenming Shu, and Anxin Wu

The Journal of Organic Chemistry 2013 Volume 78(Issue 7) pp:3132-3141

Publication Date(Web):March 12, 2013

DOI:10.1021/jo400081q

A highly efficient and stereoselective synthesis of coumarin-, 1,3-cyclohexanedione-, and 1,4-naphthoquinone-fused 2,8-dioxabicyclo[3.3.1]nonanes is described. This was achieved via a sequential Michael addition/bicyclization reaction from easily accessible 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one derivatives. Three chemical bonds (one C–C bond and two C–O bonds), two six-membered cycles, and two stereogenic centers were formed in a one-pot operation.

Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones

Co-reporter:Qinghe Gao, Xia Wu, Fengcheng Jia, Meicai Liu, Yanping Zhu, Qun Cai, and Anxin Wu

The Journal of Organic Chemistry 2013 Volume 78(Issue 6) pp:2792-2797

Publication Date(Web):February 20, 2013

DOI:10.1021/jo302754c

An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.

A Cascade Coupling Strategy for One-Pot Total Synthesis of -Carboline and Isoquinoline-Containing Natural Products and Derivatives

Co-reporter:Dr. Yan-Ping Zhu;Mei-Cai Liu;Qun Cai;Feng-Cheng Jia ; An-Xin Wu

Chemistry - A European Journal 2013 Volume 19( Issue 31) pp:10132-10137

Publication Date(Web):

DOI:10.1002/chem.201301734

Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

Co-reporter:Qing-He Gao, Zhuan Fei, Yan-Ping Zhu, Mi Lian, Feng-Cheng Jia, Mei-Cai Liu, Neng-Fang She, An-Xin Wu

Tetrahedron 2013 69(1) pp: 22-28

Publication Date(Web):

DOI:10.1016/j.tet.2012.10.072

Organic hydrogen-bonded assembly of asymmetric phenol amide molecules

Co-reporter:Lin Li;Zhuan Fei;Xiang-gao Meng;Li-ping Cao;Qun Cai

Structural Chemistry 2013 Volume 24( Issue 5) pp:1419-1428

Publication Date(Web):2013 October

DOI:10.1007/s11224-012-0168-y

The significant involvement of weak intermolecular interactions and steric and/or symmetry-related packing features was assessed with supramolecular arrays of 4-hydroxyphenyl amides in the crystal structure. The one-dimensional chain is observed in the aryl substituted 4-hydroxyphenyl amides, while alkyl analogs generate 2D or 3D arrays. A comparison of supramolecular assemblies in the similar 4-hydroxyphenyl amide compounds in the Cambridge Structural Database has been presented. It is correlated with the different steric constraints of aryl and alkyl groups to create chains, 2D sheets and 3D-interpenetrated networks in the asymmetric 4-hydroxyphenyl amides. A comprehensive analysis of crystal packing and energy features of the selected 4-hydroxyphenyl amide derivatives is reported.

Structure-based evaluation of the regioselectivity in bifurcated hydrogen bonds

Co-reporter:Lin Li;Zhuan Fei;Xiang-gao Meng;Li-ping Cao;Tao Pang

Structural Chemistry 2013 Volume 24( Issue 1) pp:97-104

Publication Date(Web):2013 February

DOI:10.1007/s11224-012-0018-y

Unsymmetrical phenolic (thio)urea molecules are investigated and compared to evaluate the regioselectivity of the bifurcated hydrogen bonds. The supramolecular aggregation can feature self-sorting homomeric α-networks through recognition between N–H···O(S) and O–H···O intermolecular hydrogen bonds. The regioselectivity of bifurcated hydrogen bond was investigated using single crystal X-ray diffraction studies, DFT calculations and Cambridge Structural Database analysis. The influence of several key variables on the fidelity of regioselectivity was described.

Convergent integration of two self-labor domino sequences: a novel method for the synthesis of oxazole derivatives from methyl ketones and benzoins

Co-reporter:Wei-Jian Xue, Qi Li, Yan-Ping Zhu, Jun-Gang Wang and An-Xin Wu

Chemical Communications 2012 vol. 48(Issue 29) pp:3485-3487

Publication Date(Web):10 Jan 2012

DOI:10.1039/C2CC18077D

A highly efficient method for the synthesis of oxazole derivatives from methyl ketones, benzoins and ammonium acetate has been established via a novel strategy—convergent integration of two self-labor domino sequences. Owing to the simple and readily available starting materials, mild reaction conditions, facile operation, and the high bioactivity of oxazole derivatives, this reaction promises diverse applications in medical chemistry. Additionally, this reaction could provide an efficient example for self-labor synthesis strategy of organic compounds.

I2 promoted domino oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles via metal-free sp3 C–H functionalization

Co-reporter:Yan-Ping Zhu, Mi Lian, Feng-Cheng Jia, Mei-Cai Liu, Jing-Jing Yuan, Qing-He Gao and An-Xin Wu

Chemical Communications 2012 vol. 48(Issue 72) pp:9086-9088

Publication Date(Web):24 Jul 2012

DOI:10.1039/C2CC34561G

An I2 promoted domino protocol was developed to construct 2-acylbenzothiazoles from simple and readily available aromatic ketones/unsaturated methyl ketones and o-aminobenzenethiols. The reaction proceeded smoothly under metal-free and peroxide-free conditions.

Direct Synthesis of Substituted Naphthalenes from 1,3-Dicarbonyl Compounds and 1,2-Bis(halomethyl)benzenes Including a Novel Rearrangement Aromatization of Benzo[c]oxepine

Co-reporter:Jun-gang Wang, Meng Wang, Jia-chen Xiang, Yan-ping Zhu, Wei-jian Xue, and An-xin Wu

Organic Letters 2012 Volume 14(Issue 23) pp:6060-6063

Publication Date(Web):November 27, 2012

DOI:10.1021/ol302950w

An unexpected rearrangement aromatization of benzo[c]oxepine has been revealed to synthesize substituted naphthalenes. This observation was further exploited to develop an efficient approach for the construction of naphthalenes from simple and commercially available 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzene compounds via a new domino reaction sequence.

I2–CF3SO3H Synergistic Promoted sp3 C–H Bond Diarylation of Aromatic Ketones

Co-reporter:Yan-ping Zhu, Feng-cheng Jia, Mei-cai Liu, Liu-ming Wu, Qun Cai, Yang Gao, and An-xin Wu

Organic Letters 2012 Volume 14(Issue 20) pp:5378-5381

Publication Date(Web):October 11, 2012

DOI:10.1021/ol302613q

An I2–CF3SO3H synergistic promoted sp3 C–H bond diarylation protocol was developed for the synthesis of 2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones. The reaction performed well in the absence of any metal and ligand. It integrated three reactions with different mechanisms (iodination, Kornblum oxidation, and hydroarylation) in a single reactor.

A Multipathway Coupled Domino Strategy: Metal-free Oxidative Cyclization for One-Pot Synthesis of 2-Acylbenzothiazoles from Multiform Substrates

Co-reporter:Yan-ping Zhu, Feng-cheng Jia, Mei-cai Liu, and An-xin Wu

Organic Letters 2012 Volume 14(Issue 17) pp:4414-4417

Publication Date(Web):August 27, 2012

DOI:10.1021/ol301921t

A multipathway coupled domino strategy has been developed for the efficient synthesis of 2-acylbenzothiazoles from multiform substrates arylethenes, arylacetylenes, 2-hydroxy-aromatic ketones, and carbinols via four distinct pathways. Through a logical coupled oxidation/heterocyclization domino process, a variety of 2-acylbenzothiazoles were synthesized free of metal in one pot.

Metal-Free sp3 C–H Bond Dual-(Het)arylation: I2-Promoted Domino Process to Construct 2,2-Bisindolyl-1-arylethanones

Co-reporter:Yan-ping Zhu, Mei-cai Liu, Feng-cheng Jia, Jing-jing Yuan, Qing-he Gao, Mi Lian, and An-xin Wu

Organic Letters 2012 Volume 14(Issue 13) pp:3392-3395

Publication Date(Web):June 26, 2012

DOI:10.1021/ol301366p

A molecular I2-promoted sp3 C–H bond dual-(het)arylation protocol was developed for the synthesis of 2,2-bisindolyl-1-arylethanones. Through a logical design, three mechanism-different reactions (iodination, Kornblum oxidation, and Friedel–Crafts reaction) were assembled in a single reactor. A variety of 2,2-bisindolyl-1-aryl ethanones were synthesized from simple and readily available aryl methyl ketones and indoles. In the reaction, metal, base, and ligand were all avoidable.

Diversity-Oriented Synthesis of Chromenes via Metal-Free Domino Reactions from Ketones and Phenols

Co-reporter:Wei-Jian Xue, Qi Li, Fang-fang Gao, Yan-ping Zhu, Jun-gang Wang, Wei Zhang, and An-Xin Wu

ACS Combinatorial Science 2012 Volume 14(Issue 8) pp:478

Publication Date(Web):June 28, 2012

DOI:10.1021/co3000506

Functionalized chromenes have been synthesized via highly selective metal-free domino reactions from ketones and phenols. 2H-Chromenes, 4H-chromenes, spiran and benzocyclopentane can be respectively prepared starting from the corresponding cyclic ketones, aryl methyl ketones, acetone, and 3-pentanone.Keywords: diversity-oriented synthesis; domino reaction; metal-free

Unsymmetrical N and/or O-bridged calixarene derivatives: synthesis, structure and encapsulation of solvent molecules in the solid state

Co-reporter:Jingjing Yuan, Yanping Zhu, Mi Lian, Qinghe Gao, Meicai Liu, Fengcheng Jia, Anxin Wu

Tetrahedron Letters 2012 Volume 53(Issue 10) pp:1222-1226

Publication Date(Web):7 March 2012

DOI:10.1016/j.tetlet.2011.12.099

Eight unsymmetrical N and/or O-bridged calixarene derivatives were obtained by 1 (naphthalene-2,7-diol), 2 (bis(4-hydroxyphenyl)methanone), 3 (4,4′-methylenedianiline), 4 (3,3′-methylenedianiline), 5 (4,4′-oxydianiline) and 6 (4,4′-(perfluoropropane-2,2-diyl)dianiline) reacting with fragment a (4,4′-bis(dichloro-s-triazinyloxy)propane-2,2-diyldibenzene) and b (N,N′-bis(dichloro-s-triazinyl)-4,4′-methylenedianiline) under very mild reaction conditions via efficient fragment coupling strategy. We also obtained the crystal structure of 1a (tetraoxocalix[2](propane-2,2-diyldibenzene,naphthalene)[2]triazine) which can form a molecular capsule by two dimers with C–H⋯N and C–H⋯O quadruple hydrogen bonds, and it has the encapsulation ability toward solvent molecules.

Convergent domino synthesis of 1,2,3-triaroylindolizines from methyl ketones and pyridines via self-division of labor strategy

Co-reporter:Yan Yang, Meng Gao, Dong-Xue Zhang, Liu-Ming Wu, Wen-Ming Shu, An-Xin Wu

Tetrahedron 2012 68(36) pp: 7338-7344

Publication Date(Web):

DOI:10.1016/j.tet.2012.06.091

Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines

Co-reporter:Mi Lian, Qi Li, Yanping Zhu, Guodong Yin, Anxin Wu

Tetrahedron 2012 68(47) pp: 9598-9605

Publication Date(Web):

DOI:10.1016/j.tet.2012.09.056

Unexpected C–C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones

Co-reporter:Qinghe Gao, Yanping Zhu, Mi Lian, Meicai Liu, Jingjing Yuan, Guodong Yin, and Anxin Wu

The Journal of Organic Chemistry 2012 Volume 77(Issue 21) pp:9865-9870

Publication Date(Web):October 12, 2012

DOI:10.1021/jo301751e

An unexpected C–C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.

Substrate-controlled and highly stereoselective synthesis of 2-aminobut-2-ene-1, 4-diones

Co-reporter:Cong Deng, Yan Yang, Meng Gao, Yan-Ping Zhu, An-Xin Wu, Jun-Rui Ma, Guo-Dong Yin

Tetrahedron 2012 68(20) pp: 3828-3834

Publication Date(Web):

DOI:10.1016/j.tet.2012.03.049

Synthesis of trisubstituted isoxazoles via in situ trapping strategy from α-nitro carbonyl compounds and methyl ketones or terminal aryl alkenes

Co-reporter:Yan Yang, Meng Gao, Cong Deng, Dong-Xue Zhang, Liu-Ming Wu, Wen-Ming Shu, An-Xin Wu

Tetrahedron 2012 68(31) pp: 6257-6262

Publication Date(Web):

DOI:10.1016/j.tet.2012.05.055

I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea

Co-reporter:Yan-Ping Zhu, Jing-Jing Yuan, Qin Zhao, Mi Lian, Qing-He Gao, Mei-Cai Liu, Yan Yang, An-Xin Wu

Tetrahedron 2012 68(1) pp: 173-178

Publication Date(Web):

DOI:10.1016/j.tet.2011.10.074

A sustainable byproduct catalyzed domino strategy: facile synthesis of α-formyloxy and acetoxy ketonesviaiodination/nucleophilic substitution/hydrolyzation/oxidation sequences

Co-reporter:Yan-Ping Zhu, Qing-He Gao, Mi Lian, Jing-Jing Yuan, Mei-Cai Liu, Qin Zhao, Yan Yang and An-Xin Wu

Chemical Communications 2011 vol. 47(Issue 47) pp:12700-12702

Publication Date(Web):31 Oct 2011

DOI:10.1039/C1CC15819H

The sustainable byproduct catalyzed domino strategy has been performed for the facile synthesis of α-formyloxy and acetoxy ketonesviaiodination/nucleophilic substitution/hydrolyzation/oxidation sequences from simple and readily available aromatic ketones/unsaturated methyl ketones.

A facile synthesis of indole–furan conjugates via integration of convergent and linear domino reactions

Co-reporter:Yan Yang, Meng Gao, Liu-Ming Wu, Cong Deng, Dong-Xue Zhang, Yang Gao, Yan-Ping Zhu, An-Xin Wu

Tetrahedron 2011 67(29) pp: 5142-5149

Publication Date(Web):

DOI:10.1016/j.tet.2011.05.058

An Efficient Synthesis of Hydantoins via Sustainable Integration of Coupled Domino Processes

Co-reporter:Meng Gao, Yan Yang, Yan-Dong Wu, Cong Deng, Wen-Ming Shu, Dong-Xue Zhang, Li-Ping Cao, Neng-Fang She, and An-Xin Wu

Organic Letters 2010 Volume 12(Issue 18) pp:4026-4029

Publication Date(Web):August 26, 2010

DOI:10.1021/ol1015948

A highly efficient synthesis of hydantoins has been developed from simple and commercially available 1,3-dicarbonyl compounds, ureas, and methyl ketones or terminal aryl alkenes. This protocol involves a sustainable integration of two coupled domino processes: iodine-promoted synthesis of unsymmetrical 1,4-enediones (domino I) and the sequential transformation into hydantoins (domino II).

Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes

Co-reporter:Meng Gao, Yan Yang, Yan-Dong Wu, Cong Deng, Li-Ping Cao, Xiang-Gao Meng and An-Xin Wu

Organic Letters 2010 Volume 12(Issue 8) pp:1856-1859

Publication Date(Web):March 22, 2010

DOI:10.1021/ol100473f

A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones.

Nanotubular non-covalent macrocycle within non-covalent macrocycle assembly: (MeOH)12 encapsulated in a molecular clip cyclododecamer

Co-reporter:Li-Ping Cao, Xiang-Gao Meng, Jiao-Yang Ding, Yun-Feng Chen, Meng Gao, Yan-Dong Wu, Yi-Tao Li, An-Xin Wu and Lyle Isaacs

Chemical Communications 2010 vol. 46(Issue 25) pp:4508-4510

Publication Date(Web):19 May 2010

DOI:10.1039/C0CC00677G

A noncovalent macrocycle-within-noncovalent macrocycle assembly is formed from twelve molecules of (±)-1 and twelve molecules of MeOH in the solid state. The H-bonded (MeOH)12 cyclododecamer assumes a crown-shaped geometry that has not previously been predicted theoretically or found experimentally.

New fluorescent probes based on supramolecular diastereomers for the detection of 2-nitrophenol

Co-reporter:Lin Li, Yichong Sun, Shuai Wang, Mingqiang Qiu, Anxin Wu

Talanta 2010 Volume 81(4–5) pp:1643-1649

Publication Date(Web):15 June 2010

DOI:10.1016/j.talanta.2010.03.018

A couple of new fluorescent probes, based on diethoxycarbonyl glycoluril, were synthesized and characterized by 1H NMR, X-ray crystal structure. The probes were found to be relatively highly fluorescence with quantum yields of 0.20 and 0.18, respectively, at room temperature in THF solution. Both of the proposed probes were tested using different phenolic compounds, showing very high selectivity and sensitivity for 2-nitrophenol by forming a 1:1 complex in THF-MeOH (9:1, v/v). Additionally, the sensors could be used for the qualitative analysis of 2-nitrophenol in real water samples.

Supramolecular Rhombic Grids Formed from Bimolecular Building Blocks

Co-reporter:Neng-Fang She ; Meng Gao ; Xiang-Gao Meng ; Guang-Fu Yang ; Johannes A. A. W. Elemans ; An-Xin Wu ;Lyle Isaacs

Journal of the American Chemical Society 2009 Volume 131(Issue 33) pp:11695-11697

Publication Date(Web):July 31, 2009

DOI:10.1021/ja904920r

A programmed assembly process produces rhombic grid networks from compounds L1−L4 in the crystal by π−π stacking interactions that generate a bimolecular grid synthon, which undergoes further NH···N hydrogen-bond-mediated assembly.

Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia

Co-reporter:Liping Cao, Jiaoyang Ding, Meng Gao, Zihua Wang, Juan Li and Anxin Wu

Organic Letters 2009 Volume 11(Issue 17) pp:3810-3813

Publication Date(Web):August 10, 2009

DOI:10.1021/ol901250c

A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH3·H2O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben−Haller−Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.

Sensor for Nitrophenol Based on a Fluorescent Molecular Clip

Co-reporter:Nengfang She, Meng Gao, Liping Cao, Anxin Wu and Lyle Isaacs

Organic Letters 2009 Volume 11(Issue 12) pp:2603-2606

Publication Date(Web):May 18, 2009

DOI:10.1021/ol900858d

We report the synthesis, X-ray crystal structure, and photophysics of a fluorescent molecular clip (1). Binding studies of 1 toward phenols 2a−j were carried out using fluorescence, 1H NMR, and IR spectroscopy, which revealed a high affinity and selectivity for 4-nitrophenol (2a) due to formation of the 1·2a complex driven by H-bonding and π−π stacking interactions.

Solvent Effect on Pseudopolymorphism of Hemicyclohexylcucurbit[6]uril

Co-reporter:Yitao Li, Lin Li, Yanping Zhu, Xianggao Meng, and Anxin Wu

Crystal Growth & Design 2009 Volume 9(Issue 10) pp:4255

Publication Date(Web):September 21, 2009

DOI:10.1021/cg9007262

Novel covalent macrocycle, hmcyCuc6, has been synthesized and its four pseudopolymorphs were reported. HmcyCuc6 is highly selective to CH2Cl2, CHCl3, and CCl4 in the crystal growth, and the selectivity of the hmcyCuc6 toward these solvent molecules may be related to the symmetry of the solvent molecules. In addition, four pseudopolymorphs can be simply controlled by changing the crystallization solvent system. To our best knowledge, the pseudopolymorphism of the cucurbit[n]uril homologues is reported for the first time.

A concise and efficient way to synthesize polyenic diones directly from α,β-unsaturated methyl ketones

Co-reporter:Meng Gao, Guodong Yin, Zihua Wang, Yandong Wu, Cheng Guo, Yuanjiang Pan, Anxin Wu

Tetrahedron 2009 65(31) pp: 6047-6049

Publication Date(Web):

DOI:10.1016/j.tet.2009.05.050

Tetrameric molecular bowl assembled from glycoluril building blocks

Co-reporter:Neng-Fang She, Xiang-Gao Meng, Meng Gao, An-Xin Wu and Lyle Isaacs

Chemical Communications 2008 (Issue 27) pp:3133-3135

Publication Date(Web):04 Apr 2008

DOI:10.1039/B800785C

Glycoluril derivative 1—whose bulky Ph–CC– substituents prevent formation of H-bonded tapes—undergoes solvent dependent assembly in the crystal; a tetrameric molecular bowl is formed by R44(24) H-bonding interactions from CH2Cl2 whereas DMF results in H-bond dimerization followed by oligomerization via C–H⋯π interactions.

Self-Assembly of Discrete and Polymeric Metal-Organic Frameworks via a Semirigid Glycoluril-Based Molecular Clip

Co-reporter:Yitao Li, Xianggao Meng, Liping Cao, Yuzhou Wang, Guodong Yin, Meng Gao, Lili Wen and Anxin Wu

Crystal Growth & Design 2008 Volume 8(Issue 5) pp:1645

Publication Date(Web):April 11, 2008

DOI:10.1021/cg701090c

Glycoluril-based molecular clip L bearing two N,N′-chelating sites and a rigid cavity has been prepared. With L, one metallomacrocycle and three metal-organic frameworks, [Cu(L)(OAc)2(H2O)·2H2O]n (1), [Co(L)2(NO3)2(H2O)2·4H2O]n (2), [Zn(L)2(NO3)2(H2O)2·7H2O]n (3), and [Cu(L)(I)·DMF]n (4) were crystallized, which display three different structure types. In 1, two ligands are arranged in a face-to-face conformation to coordinate two Cu(II) ions from opposite directions through axial positions, generating a pesudo-rectangular metallomacrocycle. Polymer 2 is an 1D double ribbons. Interestingly, each double ribbons is connected by hydrogen bond with the result that the channels are formed and run parallel to the ab diagonal, and the water chains with the symbol C4 are located within the channels. Polymer 3 exhibits the same topological morphology as polymer 2. However, each double ribbons in 3 is connected by a different type of hydrogen bond with the result that the channels are formed along the b axis. Polymer 4 is a two-dimensional (2D) tubular sheet constructed by an unprecedented [CuI]∞ column and clip ligand L. The type of the [CuI]∞ column can be described as a zigzag chain and has been rarely reported. The DMF solvent molecules are located within the channels.

Synthesis and Crystal Structure of 5,7,12,13b,13c,14-Hexahydro-1,4,-dibromo-8,11-dimethoxy-13b,13c-bis(ethoxycarbonyl)-6H,13H-5a,6a,12a,13a-tetra azbenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione

Co-reporter:Zhiguo Wang;Yuzhou Wang;Guodong Yin;Anxin Wu

Journal of Chemical Crystallography 2008 Volume 38( Issue 8) pp:591-594

Publication Date(Web):2008 August

DOI:10.1007/s10870-008-9348-4

The title compound has been synthesized by the reaction of 4 with 1,4-dimethoxybenzene. The yielded product 5 was investigated with X-ray crystallographic, NMR, EI-MS, and IR techniques. The crystal belongs to a monoclinic system, space group P21/c with unit cell parameters a = 12.7790(17) Å, b = 21.565(3) Å, c = 12.2544(16) Å, α = 90°, β = 107.014(2)°, γ = 90°, V = 3229.3(7) Å3, Z = 4, Dc = 1.661, Mr = 807.32, μ = 2.732 mm−1, F(000) = 1632, R1 = 0.0540 and wR2 = 0.0989.

Tetrameric molecular bowl assembled from glycoluril building blocks

Co-reporter:Neng-Fang She, Xiang-Gao Meng, Meng Gao, An-Xin Wu and Lyle Isaacs

Chemical Communications 2008(Issue 27) pp:NaN3135-3135

Publication Date(Web):2008/04/04

DOI:10.1039/B800785C

Glycoluril derivative 1—whose bulky Ph–CC– substituents prevent formation of H-bonded tapes—undergoes solvent dependent assembly in the crystal; a tetrameric molecular bowl is formed by R44(24) H-bonding interactions from CH2Cl2 whereas DMF results in H-bond dimerization followed by oligomerization via C–H⋯π interactions.

Nanotubular non-covalent macrocycle within non-covalent macrocycle assembly: (MeOH)12 encapsulated in a molecular clip cyclododecamer

Co-reporter:Li-Ping Cao, Xiang-Gao Meng, Jiao-Yang Ding, Yun-Feng Chen, Meng Gao, Yan-Dong Wu, Yi-Tao Li, An-Xin Wu and Lyle Isaacs

Chemical Communications 2010 - vol. 46(Issue 25) pp:NaN4510-4510

Publication Date(Web):2010/05/19

DOI:10.1039/C0CC00677G

A noncovalent macrocycle-within-noncovalent macrocycle assembly is formed from twelve molecules of (±)-1 and twelve molecules of MeOH in the solid state. The H-bonded (MeOH)12 cyclododecamer assumes a crown-shaped geometry that has not previously been predicted theoretically or found experimentally.

A concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via an unusual TBHP/Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement

Co-reporter:Zhi-Wen Zhou, Feng-Cheng Jia, Cheng Xu, Shi-Fen Jiang, Yan-Dong Wu and An-Xin Wu

Chemical Communications 2017 - vol. 53(Issue 6) pp:NaN1059-1059

Publication Date(Web):2016/12/19

DOI:10.1039/C6CC09376K

An efficient transition-metal-free cascade reaction has been developed for the facile synthesis of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one derivatives from commercially available isatins and 2-haloaryl isothiocyanates. A preliminary mechanistic study suggested an interrupted Dimroth rearrangement was the key step for the successful transformation.

I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

Co-reporter:Xia Wu, Xiao Geng, Peng Zhao, Jingjing Zhang, Yan-dong Wu and An-xin Wu

Chemical Communications 2017 - vol. 53(Issue 24) pp:NaN3441-3441

Publication Date(Web):2017/02/28

DOI:10.1039/C6CC10275A

An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the CN cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

A sustainable byproduct catalyzed domino strategy: facile synthesis of α-formyloxy and acetoxy ketonesviaiodination/nucleophilic substitution/hydrolyzation/oxidation sequences

Co-reporter:Yan-Ping Zhu, Qing-He Gao, Mi Lian, Jing-Jing Yuan, Mei-Cai Liu, Qin Zhao, Yan Yang and An-Xin Wu

Chemical Communications 2011 - vol. 47(Issue 47) pp:NaN12702-12702

Publication Date(Web):2011/10/31

DOI:10.1039/C1CC15819H

The sustainable byproduct catalyzed domino strategy has been performed for the facile synthesis of α-formyloxy and acetoxy ketonesviaiodination/nucleophilic substitution/hydrolyzation/oxidation sequences from simple and readily available aromatic ketones/unsaturated methyl ketones.

Convergent integration of two self-labor domino sequences: a novel method for the synthesis of oxazole derivatives from methyl ketones and benzoins

Co-reporter:Wei-Jian Xue, Qi Li, Yan-Ping Zhu, Jun-Gang Wang and An-Xin Wu

Chemical Communications 2012 - vol. 48(Issue 29) pp:NaN3487-3487

Publication Date(Web):2012/01/10

DOI:10.1039/C2CC18077D

A highly efficient method for the synthesis of oxazole derivatives from methyl ketones, benzoins and ammonium acetate has been established via a novel strategy—convergent integration of two self-labor domino sequences. Owing to the simple and readily available starting materials, mild reaction conditions, facile operation, and the high bioactivity of oxazole derivatives, this reaction promises diverse applications in medical chemistry. Additionally, this reaction could provide an efficient example for self-labor synthesis strategy of organic compounds.

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones

Co-reporter:Feng-Cheng Jia, Cheng Xu, Qun Cai and An-Xin Wu

Chemical Communications 2014 - vol. 50(Issue 69) pp:NaN9916-9916

Publication Date(Web):2014/06/27

DOI:10.1039/C4CC03420A

A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermolecular C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction.

Intramolecular decarboxylative coupling as the key step in copper-catalyzed domino reaction: facile access to 2-(1,3,4-oxadiazol-2-yl)aniline derivatives

Co-reporter:Cheng Xu, Feng-Cheng Jia, Qun Cai, Deng-Kui Li, Zhi-Wen Zhou and An-Xin Wu

Chemical Communications 2015 - vol. 51(Issue 30) pp:NaN6632-6632

Publication Date(Web):2015/03/05

DOI:10.1039/C5CC01116G

A copper-catalyzed domino protocol for the synthesis of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives has been developed from simple and available isatins and hydrazides. This domino process integrated consecutive condensation, base-promoted ring-opening and the key copper-catalyzed decarboxylative coupling for intramolecular C–O bond formation.

Synthesis of α-iodoketals from methyl ketones via sustainable and orthogonal tandem catalysis

Co-reporter:Yan Yang, Meng Gao, Wen-Ming Shu, Liu-Ming Wu, Dong-Xue Zhang and An-Xin Wu

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 7) pp:NaN1233-1233

Publication Date(Web):2012/12/19

DOI:10.1039/C2OB27028E

A highly efficient method for the direct synthesis of α-iodoketals from methyl ketones has been developed via sustainable integration of orthogonal tandem catalytic reactions: copper(II) oxide catalyzed iodination reaction and the subsequent excess or regenerated iodine catalyzed regioselective ketalization reaction.

Organopromoted direct synthesis of 6-iodo-3-methylthioimidazo[1,2-a]pyridines via convergent integration of three self-sorting domino sequences

Co-reporter:Shan Liu, Hailing Xi, Jingjing Zhang, Xia Wu, Qinghe Gao and Anxin Wu

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 33) pp:NaN8811-8811

Publication Date(Web):2015/07/17

DOI:10.1039/C5OB01313E

An NH2CN-promoted convergent integration of three self-sorting domino sequences is described for the construction of 6-iodo-3-methylthioimidazo[1,2-a]pyridines from aryl methyl ketones and 2-aminopyridines. This strategy allows the construction of an imidazo[1,2-a]pyridine ring along with methylthiolation at C-3 and iodination at C-6. Preliminary mechanistic studies indicate that this process terminates at the iodination stage without Kornblum oxidation in the presence of I2 and DMSO.

Brønsted acid promoted addition–cyclization and C–C bond cleavage: a convenient synthesis of 2-amino-5-aroylmethylthiazoles derivatives

Co-reporter:Fan Ni, Yan Yang, Wen-Ming Shu, Jun-Rui Ma and An-Xin Wu

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 46) pp:NaN9470-9470

Publication Date(Web):2014/10/20

DOI:10.1039/C4OB01519C

A Brønsted acid promoted C–C bond cleavage method for the synthesis of novel 2-amino-5-aroylmethylthiazole derivatives has been directly developed from 1,4-enediones and thioureas through self-sequenced thio-Michael-addition, intramolecular selective cyclization, dehydration/aromatization, and C–C bond cleavage reactions. It is noteworthy that this reaction has significant advantages in simple reagents, under environmentally benign conditions and with excellent yields. This highly efficient method is also a highly attractive alternative for the preparation of PLTP, CETP inhibitors and novel biheterocycles.

I2 promoted domino oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles via metal-free sp3 C–H functionalization

Co-reporter:Yan-Ping Zhu, Mi Lian, Feng-Cheng Jia, Mei-Cai Liu, Jing-Jing Yuan, Qing-He Gao and An-Xin Wu

Chemical Communications 2012 - vol. 48(Issue 72) pp:NaN9088-9088

Publication Date(Web):2012/07/24

DOI:10.1039/C2CC34561G

An I2 promoted domino protocol was developed to construct 2-acylbenzothiazoles from simple and readily available aromatic ketones/unsaturated methyl ketones and o-aminobenzenethiols. The reaction proceeded smoothly under metal-free and peroxide-free conditions.

Auto-tandem catalysis: synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones via copper-catalyzed aza-Michael addition–aerobic dehydrogenation–intramolecular amidation

Co-reporter:Yan Yang, Wen-Ming Shu, Shang-Bo Yu, Fan Ni, Meng Gao and An-Xin Wu

Chemical Communications 2013 - vol. 49(Issue 17) pp:NaN1731-1731

Publication Date(Web):2013/01/11

DOI:10.1039/C3CC38131E

A copper-catalyzed domino synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed from 1,4-enediones and 2-aminoheterocycles with air as the oxidant.

Formamidine hydrochloride as an amino surrogate: I2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N–H) α-ketoamides

Co-reporter:Shan Liu, Qinghe Gao, Xia Wu, Jingjing Zhang, Kerong Ding and Anxin Wu

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 8) pp:NaN2242-2242

Publication Date(Web):2015/01/05

DOI:10.1039/C4OB02591A

A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones with formamidine hydrochloride has been developed. This reaction represents a novel strategy for the synthesis of free (N–H) α-ketoamides. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/amidation/oxidation/decarbonylation mechanism was proposed.

Efficient approach to 2-hydroxy-2,3-dihydrofuran derivatives and its application for the synthesis of novel 4-(1H-pyrazol-4-yl)pyridazines

Co-reporter:Jun-Rui Ma, Wen-Ming Shu, Kai-Lu Zheng, Fan Ni, Guo-Dong Yin and An-Xin Wu

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 17) pp:NaN4980-4980

Publication Date(Web):2015/03/30

DOI:10.1039/C5OB00163C

A highly efficient method for the synthesis of 2-hydroxy-2,3-dihydrofuran derivatives from 1,4-enediones and phenacyl pyridinium halides via a domino reaction has been developed. This is a simple and beneficial strategy for the construction of 2-hydroxy-2,3-dihydrofuran compounds from readily available starting materials under mild conditions. Moreover, the application of this reaction provides a straightforward and practical route for the synthesis of the novel 4-(1H-pyrazol-4-yl)pyridazine skeleton.

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles

Co-reporter:Jiachen Xiang, Jungang Wang, Miao Wang, Xianggao Meng and Anxin Wu

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 14) pp:NaN4247-4247

Publication Date(Web):2015/02/25

DOI:10.1039/C5OB00025D

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones.

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Abstract

Abstract