Changsheng Yao

Name:

Organization: Jiangsu Normal University

Department: School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials

Title:

Chemicals
References

NHC-catalyzed [4 + 2] annulation of 2-bromo-2-enals with acylhydrazones: enantioselective synthesis of δ-lactams

Co-reporter:Baomin Sun;Lijiu Gao;Shide Shen;Chenxia Yu;Tuanjie Li;Yuanwei Xie

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 4) pp:991-997

Publication Date(Web):2017/01/25

DOI:10.1039/C6OB02253G

An asymmetric assembly of δ-lactams was realized via the NHC-catalyzed formal [4 + 2] annulation of acylhydrazones and 2-bromo-2-enals bearing γ-H. The advantages of this protocol include high enantioselectivity, good yields, mild reaction conditions and potential biological significance of the final products.

NHC-catalyzed regiodivergent syntheses of difunctionalized 3-pyrazolidinones from α-bromoenal and monosubstituted hydrazine

Co-reporter:Chenxia Yu;Shide Shen;Ligen Jiang;Jing Li;Yumiao Lu;Tuanjie Li

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 43) pp:9149-9155

Publication Date(Web):2017/11/07

DOI:10.1039/C7OB02041D

A formal [3 + 2] annulation of α-bromoenal with monosubstituted hydrazine could give 1,5 or 2,5-difunctionalized 3-pyrazolidinone regiodivergently by tuning the structure of the N-Heterocyclic Carbene (NHC) catalyst. Moderate to high yields, mild reaction conditions, good regioselectivity and potential biological significance of the final product have made this protocol attractive for the assembly of 3-pyrazolidinone.

N-Heterocyclic Carbene-Catalyzed [4 + 2] Cyclization of Saturated Carboxylic Acid with o-Quinone Methides through in Situ Activation: Enantioselective Synthesis of Dihydrocoumarins

Co-reporter:Yuanfeng Wang, Jian Pan, Jingjiao Dong, Chenxia Yu, Tuanjie Li, Xiang-Shan WangShide Shen, Changsheng Yao

The Journal of Organic Chemistry 2017 Volume 82(Issue 3) pp:

Publication Date(Web):January 11, 2017

DOI:10.1021/acs.joc.6b02444

An N-heterocyclic carbene (NHC)-catalyzed formal [4 + 2] synthesis of dihydrocoumarins was realized from saturated carboxylic acids and o-quinone methides via an in situ activation strategy. This protocol results in excellent diastereoselectivity and enantioselectivity and good yields and uses readily available and inexpensive starting materials.

N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of α,β-unsaturated carboxylic acids bearing γ-H with isatins: an enantioselective synthesis of spirocyclic oxindole–dihydropyranones

Co-reporter:Ling Zhu, Chenxia Yu, Tuanjie Li, Yuhong Wang, Yinan Lu, Wenjing Wang and Changsheng Yao

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 4) pp:1485-1491

Publication Date(Web):16 Dec 2015

DOI:10.1039/C5OB02160J

An NHC-catalyzed asymmetric [4 + 2] annulation of isatins and α,β-unsaturated carboxylic acids bearing γ-H gave spirocyclic oxindole–dihydropyranones successfully via an in situ activation strategy. This protocol featured easy availability of raw materials, good yields and excellent enantioselectivities (up to 99% ee).

A facile one-pot synthesis of 2,3-diarylated benzo[b]furans via relay NHC and palladium catalysis

Co-reporter:Yanyan Jia, Tuanjie Li, Chenxia Yu, Bo Jiang and Changsheng Yao

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 6) pp:1982-1987

Publication Date(Web):05 Jan 2016

DOI:10.1039/C5OB02336J

An efficient one-pot synthesis of 2,3-diarylated benzo[b]furans was realized through the relay catalysis of N-Heterocyclic Carbene (NHC) and palladium from substituted 2′-bromodiphenylbromomethanes and aryl aldehydes. The easy availability of the starting materials, good compatibility of catalysts, convergent assembly and concomitant modification of the target scaffold, and potential utilization value of the products make this strategy attractive in organic synthesis.

N-Heterocyclic carbene-triggered transition-metal-free synthesis of 2,3-disubstituted benzofuran derivatives

Co-reporter:Yuanwei Xie, Chenxia Yu, Yonglei Que, Tuanjie Li, Yuhong Wang, Yinan Lu, Wenjing Wang, Shide Shen and Changsheng Yao

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 27) pp:6463-6469

Publication Date(Web):31 May 2016

DOI:10.1039/C6OB00363J

An NHC-triggered, transition-metal-free strategy for the efficient synthesis of 2,3-disubstituted benzofuran derivatives in moderate to excellent yields from aryl or alkyl aldehydes and o-quinone methides has been developed. This method features mild reaction conditions, operational simplicity, broad substrate scope and convergent assembly.

An Enantioselective Assembly of Dihydropyranones through an NHC/LiCl-Mediated in situ Activation of ,-Unsaturated Carboxylic Acids

Co-reporter:Yonglei Que;Yinan Lu;Wenjing Wang;Yuhong Wang;Haotian Wang;Chenxia Yu;Tuanjie Li;Xiang-Shan Wang;Shide Shen

Chemistry – An Asian Journal 2016 Volume 11( Issue 5) pp:678-681

Publication Date(Web):

DOI:10.1002/asia.201501353

Abstract

A straightforward N-heterocyclic carbene (NHC)/LiCl-mediated synthesis of dihydropyranones from α,β-unsaturated carboxylic acids and 1,3-dicarbonyl compounds was realized through the in situ activation strategy. The key advantages of this protocol include ready availability and high stability of starting materials, good yields, and excellent enantioselectivity.

Cover Picture: An Enantioselective Assembly of Dihydropyranones through an NHC/LiCl-Mediated in situ Activation of ,-Unsaturated Carboxylic Acids (Chem. Asian J. 5/2016)

Co-reporter:Yonglei Que;Yinan Lu;Wenjing Wang;Yuhong Wang;Haotian Wang;Chenxia Yu;Tuanjie Li;Xiang-Shan Wang;Shide Shen

Chemistry – An Asian Journal 2016 Volume 11( Issue 5) pp:

Publication Date(Web):

DOI:10.1002/asia.201600174

An N-Heterocyclic Carbene-Catalyzed Oxidative γ-Aminoalkylation of Saturated Carboxylic Acids through in Situ Activation Strategy: Access to δ-Lactam

Co-reporter:Yonglei Que, Yuanwei Xie, Tuanjie Li, Chenxia Yu, Shujiang Tu, and Changsheng Yao

Organic Letters 2015 Volume 17(Issue 24) pp:6234-6237

Publication Date(Web):December 8, 2015

DOI:10.1021/acs.orglett.5b03223

An N-Heterocyclic Carbene (NHC)-catalyzed oxidative formal [4 + 2] annulation of acylhydrazones with saturated carboxylic acids bearing γ-H to assemble δ-lactams featuring a chiral carbon stereogenic center was developed through an in situ activation strategy. The ready availability of the starting materials, excellent enantioselectivity, facile assembly, high yields, and potential biological significance of the final products make this protocol an attractive alternative for the construction of the pyridinone scaffold.

N-heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole

Co-reporter:Yuanwei Xie, Yonglei Que, Tuanjie Li, Ling Zhu, Chenxia Yu and Changsheng Yao

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 6) pp:1829-1835

Publication Date(Web):03 Dec 2014

DOI:10.1039/C4OB01706D

A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon in moderate to good yields with high diastereoselectivities. The easy availability of the starting materials, the concise assembly and the potential utilization value of the products make this strategy attractive in molecular biology and pharmacy.

An efficient synthesis of [1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel thiazapodophyllotoxin analogues with potential anticancer activity

Co-reporter:Tuanjie Li, Ting Lu, Chenxia Yu, Changsheng Yao

Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 7) pp:1417-1419

Publication Date(Web):1 April 2015

DOI:10.1016/j.bmcl.2015.02.047

A catalyst-free synthesis of 6,9-dihydro-[1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel analogues of podophyllotoxins was developed by a three-component reaction of aldehydes, ethyl 2,4-dioxotetrahydrothiophene-3-carboxylate and 3,4-(methylenedioxy)aniline. This methodology not only provides new chemical library for the screening of anticancer activity, but also features excellent isolated yields, short reaction time, simple work up procedure and little environmental impact.

An NHC-Catalyzed In Situ Activation Strategy to -Functionalize Saturated Carboxylic Acid: An Enantioselective Formal [3+2] Annulation for Spirocyclic Oxindolo--butyrolactones

Co-reporter:Yuanwei Xie; Chenxia Yu;Tuanjie Li;Dr. Shujiang Tu ;Dr. Changsheng Yao

Chemistry - A European Journal 2015 Volume 21( Issue 14) pp:5355-5359

Publication Date(Web):

DOI:10.1002/chem.201500345

Abstract

An in situ NHC-catalyzed activation strategy to β-functionalize saturated carboxylic acid was developed. This asymmetric formal [3+2] annulation could deliver spirocyclic oxindolo-γ-butyrolactones from saturated carboxylic acid and isatin in good yields with high to excellent enantioselectivities. The easy availability of the starting materials, direct installation of functional units at unreactive carbon atom and the convergent assembly make this protocol attractive in the field of organic synthesis.

Enantioselective Assembly of Spirocyclic Oxindole-dihydropyranones through NHC-Catalyzed Cascade Reaction of Isatins with N-Hydroxybenzotriazole Esters of α,β-Unsaturated Carboxylic Acid

Co-reporter:Yonglei Que, Tuanjie Li, Chenxia Yu, Xiang-Shan Wang, and Changsheng Yao

The Journal of Organic Chemistry 2015 Volume 80(Issue 6) pp:3289-3294

Publication Date(Web):February 18, 2015

DOI:10.1021/jo502920w

An NHC-catalyzed formal [4 + 2] reaction of isatins with N-hydroxybenzotriazole ester of α,β-unsaturated carboxylic acids bearing γ-H to construct spirocyclic oxindole-dihydropyranones featuring a chiral tetrasubstituted carbon stereogenic center was developed. The high enantioselectivity, the ready availability of the raw materials, the facile assembly, and the potential biological significance of the final products make this protocol an attractive alternative for the synthesis of spirocyclic heterocycles.

Electrocatalytic multicomponent transformation of cyclopentane-1,3-dione, aldehydes and malononitrile: an efficient way to cyclopenta[b]pyran derivatives

Co-reporter:Liang Wang;Jie Gao;Lirong Wan;Ying Wang

Research on Chemical Intermediates 2015 Volume 41( Issue 5) pp:2775-2784

Publication Date(Web):2015 May

DOI:10.1007/s11164-013-1387-6

An electrochemical synthesis of 4-substituted-cyclopenta[b]pyran derivatives through the one-pot condensation of cyclopentane-1,3-dione, malononitrile, and aldehydes is reported. The reaction is carried out in an undivided cell in the presence of sodium bromide as a supporting electrolyte. Notably, the presented method features high efficiency, excellent yield, and simple experimental procedure.

N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirocyclic Oxindole–Dihydropyranones

Co-reporter:Zhaoxin Xiao, Chenxia Yu, Tuanjie Li, Xiang-Shan Wang, and Changsheng Yao

Organic Letters 2014 Volume 16(Issue 14) pp:3632-3635

Publication Date(Web):July 2, 2014

DOI:10.1021/ol501224p

Under the cooperative catalysis of NHC/Lewis acid, the mild, straightforward [4 + 2] annulation of α-bromo-α,β-unsaturated aldehydes bearing γ-H with isatin derivatives gave spirocyclic oxindole–dihydropyranones stereoselectively. This approach is particularly attractive due to the concise construction, avoidance of external oxidants, and the potential utilization value of final products in molecular biology and pharmacy.

NHC-catalyzed oxidative γ-addition of α,β-unsaturated aldehydes to isatins: a high-efficiency synthesis of spirocyclic oxindole-dihydropyranones

Co-reporter:Rui Liu, Chenxia Yu, Zhaoxin Xiao, Tuanjie Li, Xiangshan Wang, Yuanwei Xie and Changsheng Yao

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 12) pp:1885-1891

Publication Date(Web):06 Jan 2014

DOI:10.1039/C3OB42008F

This manuscript discloses an efficient construction of the spirocyclic oxindole-dihydropyranone scaffold via the N-heterocyclic carbene (NHC)-catalyzed oxidative γ-functionalization of α,β-unsaturated aldehydes bearing γ-H with isatin derivatives. The ready availability of the starting materials, easy work-up, mild reaction conditions and the potential utilization value of the products make this strategy attractive.

One-Pot Three-Component Synthesis of Benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-one Derivatives

Co-reporter:Chenxia Yu;Honghong Zhang;Tuanjie Li;Bingbin Qin;Jun Lu;Donglin Wang

Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 3) pp:702-705

Publication Date(Web):

DOI:10.1002/jhet.1727

A series of novel benzo[f]thiopyrano[3,4-b]quinolin-11(8H)-one derivatives were synthesized via the reaction of aryl aldehyde, 2H-thiopyran-3,5(4H,6H)-dione, and β-naphthylamine in glacial acetic acid. This protocol features mild reaction conditions, high yields, and short reaction time.

A Catalyst-Free Aqueous Synthesis of 2-Amino-7,9-dihydrothieno[3,2:5,6]pyrido[2,3-d]pyrimidine-4,6(3H,5H)-dione Derivatives

Co-reporter:Changsheng Yao;Ting Lu;Chenxia Yu;Xiangshan Wang;Tuanjie Li

Journal of Heterocyclic Chemistry 2014 Volume 51( Issue S1) pp:E163-E166

Publication Date(Web):

DOI:10.1002/jhet.1915

A series of novel 7,9-dihydrothieno[3′,2′:5,6]pyrido[2,3-d]pyrimidine-4,6(3H,5H)-dione derivatives were synthesized efficiently via the catalyst-free reaction of aldehyde, ethyl 2,4-dioxotetrahydrothiophene-3-carboxylate, and 2,6-diaminopyrimidine-4(3H)-one through the sequence of deethoxycarbonylation and three-component condensation in aqueous media. This protocol featured mild reaction conditions, high yields, easy work-up, and environmentally friendly procedure.

An Efficient Synthesis and Fluorescent Properties of Pyrazole[3,4-b]thieno[2,3-e]pyridine Derivatives

Co-reporter:Chang-Sheng Yao;Ke Lu;Bin Song;Bin Liu;Tuan-Jie Li;Chen-Xia Yu

Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 6) pp:1807-1810

Publication Date(Web):

DOI:10.1002/jhet.1888

A simple and efficient method for the synthesis of pyrazole[3,4-b]thieno[2,3-e]pyridine derivatives via the sequence of three-component, catalyst-free, and solvent-free condensation and oxidation was described. The products feature a donor-π-conjugated acceptor fluorescent activity system, and the fluorescence emission wavelength was measured in methanol. Some products were fluorescent in solution emitting at blue light (λ_em = 430–505 nm).

An aqueous, catalyst-free and three-component synthesis of 6-amino-3-(trifluoromethyl)-1,4-dihydro-1-phenyl-4-arylpyrano[2,3-c]pyrazole-5-carbonitriles

Co-reporter:Chenxia Yu;Tuanjie Li

Research on Chemical Intermediates 2014 Volume 40( Issue 4) pp:1537-1544

Publication Date(Web):2014 April

DOI:10.1007/s11164-013-1058-7

A concise synthesis of 6-amino-4-aryl-3-(trifluoromethyl)-1,4-dihydro-1-phenylpyrano[2,3-c]pyrazole-5-carbonitriles was performed effectively in aqueous media without catalyst by the reaction of aryl aldehydes, malononitrile, and 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one. This method has the advantages of mild condition, avoidance of the use of catalysts, high yields, and environmentally benign procedure.

A facile synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines through NHC-catalyzed cascade annulations

Co-reporter:Changsheng Yao, Weihui Jiao, Zhaoxin Xiao, Yuanwei Xie, Tuanjie Li, Xiangshan Wang, Rui Liu and Chenxia Yu

RSC Advances 2013 vol. 3(Issue 27) pp:10801-10805

Publication Date(Web):24 Apr 2013

DOI:10.1039/C3RA41935E

A new efficient approach for the synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines with biological significance was successfully developed through a NHC-catalyzed cascade C–C bond and C–N bond formation process. This new alternative approach for the assembly of these multi-functionalized nitrogen bridgehead-fused heterocycles features mild conditions, moderate to high yields and operational simplicity.

N-Heterocyclic-Carbene-Catalyzed Reaction of -Bromo-,-Unsaturated Aldehyde or ,-Dibromoaldehyde with Isatins: An Efficient Synthesis of Spirocyclic OxindoleDihydropyranones

Co-reporter:Dr. Changsheng Yao;Zhaoxin Xiao;Rui Liu;Dr. Tuanjie Li;Weihui Jiao; Chenxia Yu

Chemistry - A European Journal 2013 Volume 19( Issue 2) pp:456-459

Publication Date(Web):

DOI:10.1002/chem.201202655

Solvent-free synthesis of 14-Aryl-14H-dibenzo[a,j]xanthenes catalyzed by recyclable and reusable iron(III) triflate

Co-reporter:Yang Cao;Bingbin Qin;Honghong Zhang

Research on Chemical Intermediates 2013 Volume 39( Issue 7) pp:3055-3062

Publication Date(Web):2013 September

DOI:10.1007/s11164-012-0818-0

A solvent-free and efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes through the one-pot condensation of β-naphthol and aldehydes catalyzed by recyclable and reusable Iron(III) triflate was reported. Notably, the presented method features short reaction time, excellent yield, and simple experimental procedure.

A pseudo multi-component electrochemical synthesis of spiro dihydrofuran derivatives

Co-reporter:Changsheng Yao, Ying Wang, Tuanjie Li, Chenxia Yu, Liang Li, Chao Wang

Tetrahedron 2013 69(49) pp: 10593-10597

Publication Date(Web):

DOI:10.1016/j.tet.2013.10.056

N-Heterocyclic carbene-triggered transition-metal-free synthesis of 2,3-disubstituted benzofuran derivatives

Co-reporter:Yuanwei Xie, Chenxia Yu, Yonglei Que, Tuanjie Li, Yuhong Wang, Yinan Lu, Wenjing Wang, Shide Shen and Changsheng Yao

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 27) pp:NaN6469-6469

Publication Date(Web):2016/05/31

DOI:10.1039/C6OB00363J

NHC-catalyzed oxidative γ-addition of α,β-unsaturated aldehydes to isatins: a high-efficiency synthesis of spirocyclic oxindole-dihydropyranones

Co-reporter:Rui Liu, Chenxia Yu, Zhaoxin Xiao, Tuanjie Li, Xiangshan Wang, Yuanwei Xie and Changsheng Yao