Co-reporter:Wei Lin, Yong-Xiang Zheng, Zhan Xun, Zhi-Bin Huang, and Da-Qing Shi
ACS Combinatorial Science November 13, 2017 Volume 19(Issue 11) pp:708-708
Publication Date(Web):October 6, 2017
DOI:10.1021/acscombsci.7b00126
A microwave-assisted regioselective synthesis of 3-functionalized indole derivatives via a three-component domino reaction of anilines, arylglyoxal monohydrates, and cyclic 1,3-dicarbonyl compounds is described. The main advantages of this protocol are short reaction times, practical simplicity, its metal-free nature, the availability of starting materials, green solvents, and high regioselectivity.Keywords: indole; microwave-assisted; three-component reaction;
Co-reporter:Li Zhang, Chao Wang, Jian Han, Zhi-Bin Huang, and Yingsheng Zhao
The Journal of Organic Chemistry 2016 Volume 81(Issue 12) pp:5256-5262
Publication Date(Web):May 23, 2016
DOI:10.1021/acs.joc.6b00932
Pd-catalyzed regioselective coupling of β-C(sp2)–H bonds in aromatic amines protected by oxalyl amide with carbon monoxide is reported. The reaction could tolerate various functional groups and could afford good to excellent yields of the corresponding 3,4-dihydroisoquinolinone derivatives. Remarkably, it could also tolerate β-arylethylamino acid and thiopheneethylamine derivatives, thus showing their potential for producing several important units for bioactive compound synthesis.
Co-reporter:Lei Fu;Wei Lin;Da-Qing Shi
Journal of Heterocyclic Chemistry 2015 Volume 52( Issue 4) pp:1075-1081
Publication Date(Web):
DOI:10.1002/jhet.2133
A facile and efficient one-pot procedure for the preparation of indeno[1,2-b]indole derivatives via three-component domino reaction of ninhydrin, enaminones, and malononitrile catalyzed by L-proline is described. In this reaction, two rings and four bonds were formed by one-pot.
Co-reporter:Wei Lin;Minghua Hu;Xian Feng;Chengpao Cao;Zhibin Huang;Daqing Shi
Journal of Heterocyclic Chemistry 2015 Volume 52( Issue 4) pp:1170-1174
Publication Date(Web):
DOI:10.1002/jhet.2221
A mild and efficient synthesis of 2-arylindazole derivatives via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent (TiCl4/Sm/Et3N) has been developed. The attractive features of the current method include an N–N bond formation and the selective reduction of the C = N bond and nitro group, both of which were easily achieved in one-pot by controlling the pH of the reaction mixture.
Co-reporter:Jian Han, Yongxiang Zheng, Chao Wang, Yan Zhu, Da-Qing Shi, Runsheng Zeng, Zhi-Bin Huang, and Yingsheng Zhao
The Journal of Organic Chemistry 2015 Volume 80(Issue 18) pp:9297-9306
Publication Date(Web):August 26, 2015
DOI:10.1021/acs.joc.5b00968
A method for palladium-catalyzed oxalyl amide-directed arylation of α-unsubstituted aliphatic amines with aryl iodides has been developed. A wide variety of aryl iodides are tolerated in this transformation, affording various γ-arylpropylamine derivatives. Heterocyclic iodides can also be competent reagents in this γ-C(sp3)–H bonds transformation.
Co-reporter:Jian-Jun Wang, Xian Feng, Zhan Xun, Da-Qing Shi, and Zhi-Bin Huang
The Journal of Organic Chemistry 2015 Volume 80(Issue 16) pp:8435-8442
Publication Date(Web):July 20, 2015
DOI:10.1021/acs.joc.5b01314
A simple and efficient one-pot construction of pyrazolo[3,4-e]indolizine derivatives via a diethylamine-catalyzed three-component domino reaction of arylglyoxals, cyclic 1,3-diones, and 5-aminopyrazoles under microwave irradiation is described. In this one-pot transformation, seven bonds and two new rings are efficiently formed. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional recrystallization or chromatography purification methods.
Co-reporter:Jian Han, Pei Liu, Chao Wang, Qian Wang, Jingyu Zhang, Yanwei Zhao, Daqing Shi, Zhibin Huang, and Yingsheng Zhao
Organic Letters 2014 Volume 16(Issue 21) pp:5682-5685
Publication Date(Web):October 16, 2014
DOI:10.1021/ol502745g
A successful protocol has been developed for δ-arylation of β-arylethamines at the ortho position under mild conditions. The newly developed methodology first presents broad substrate scope, great functional group tolerance, and good to excellent yield in the synthesis of substituted β-arylethylamines. The transformation represents a practical advantage of oxalyl amide in assistance with C–H functionalization at a remote position.
Co-reporter:Lei Fu, Wei Lin, Ming-Hua Hu, Xue-Cheng Liu, Zhi-Bin Huang, and Da-Qing Shi
ACS Combinatorial Science 2014 Volume 16(Issue 5) pp:238
Publication Date(Web):March 26, 2014
DOI:10.1021/co4001524
A facile and efficient one-pot procedure for the preparation of functionalized benzo[b][1,8]naphthyridine derivatives by three-component reaction of 2-chloroquinoline-3-carbaldehyde, 1,3-dicarbonyl compounds, and enaminones catalyzed by l-proline is described. This new protocol has the advantages of environmental friendliness, good yields, and convenient operation.Keywords: benzo[b][1,8]naphthyridine; l-proline; three-component reaction
Co-reporter:Wei Lin, Ming-Hua Hu, Xian Feng, Lei Fu, Cheng-Pao Cao, Zhi-Bin Huang, Da-Qing Shi
Tetrahedron Letters 2014 Volume 55(Issue 14) pp:2238-2242
Publication Date(Web):2 April 2014
DOI:10.1016/j.tetlet.2014.02.072
The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.
Co-reporter:Li-Li Li;Hui-Yuan Wang;Wei Lin;Da-Qing Shi
Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 6) pp:1778-1784
Publication Date(Web):
DOI:10.1002/jhet.1882
A improved and efficient procedure for the synthesis of pyrrolo[2,3,4-kl]acridin-1-one derivatives via the reaction of isatin and enaminone catalyzed by ceric ammonium nitrate under ultrasonic condition has been developed. Compared with the conventional methods, the remarkable advantages of this method are mild reaction conditions, operational simplicity, higher yield, and shorter reaction times.
Co-reporter:Ming-Hua Hu;Wei Lin;Cheng-Pao Cao, ;Da-Qing Shi
Journal of Heterocyclic Chemistry 2014 Volume 51( Issue S1) pp:E227-E233
Publication Date(Web):
DOI:10.1002/jhet.2023
A simple and efficient synthesis of pyrrolo[2,3,4-kl]acridine-1-one derivatives via the cascade reaction of isatins with enaminones catalyzed by silica sulfuric acid (SSA) has been established. In this reactions, SSA shows a highly catalytic nature: easy to handle procedure, short reaction time, recycle exploitation, insensitivity to air and moisture, and excellent isolated yields. The catalyst could be recycled at least five times.
Co-reporter:Xue-Cheng Liu;Wei Lin;Hui-Yan Wang;Da-Qing Shi
Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 4) pp:1036-1044
Publication Date(Web):
DOI:10.1002/jhet.2104
A series of chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one derivatives was easily and efficiently synthesized by the reaction of 2H-chromen-2-ones with pyrazol-5-amines catalyzed by CuCl2⋅2H2O in ethanol. This protocol has the advantages of mild reaction conditions, easy work-up, and high yields. These compounds were showed to have high fluorescence quantum yields, which mentioned their value as luminescence or fluorescence probe.
Co-reporter:Jun-Die Hu, Cheng-Pao Cao, Wei Lin, Ming-Hua Hu, Zhi-Bin Huang, and Da-Qing Shi
The Journal of Organic Chemistry 2014 Volume 79(Issue 17) pp:7935-7944
Publication Date(Web):July 31, 2014
DOI:10.1021/jo501049m
A series of novel polyfunctionalized pyrido[2,3-b]indoles were synthesized by three- or four-component domino reactions under microwave irradiation. This protocol has the advantages of readily available starting materials, short reaction times, high yields, easy workup, and high chemo- and regioselectivities.
Co-reporter:Huiyan Wang, Xuecheng Liu, Xian Feng, Zhibin Huang and Daqing Shi
Green Chemistry 2013 vol. 15(Issue 12) pp:3307-3311
Publication Date(Web):25 Sep 2013
DOI:10.1039/C3GC41799A
A concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives via a four-component reaction of 4-hydroxycoumarin, arylglyoxal monohydrate, dialkyl but-2-ynedioate and amines under catalyst-free conditions in an environmentally friendly medium (ethanol) is described. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional chromatography and recrystallization purification methods.
Co-reporter:Xian Feng, Qian Wang, Wei Lin, Guo-Lan Dou, Zhi-Bin Huang, and Da-Qing Shi
Organic Letters 2013 Volume 15(Issue 10) pp:2542-2545
Publication Date(Web):May 1, 2013
DOI:10.1021/ol4010382
A highly efficient, catalyst-free synthesis of polysubstituted pyrroles by means of a novel four-component domino reaction of an arylglyoxal monohydrate, an aniline, a dialkyl but-2-ynedioate, and malononitrile is reported. This transformation proceeded via a 6,6a-dihydrofuro[2,3-b]pyrrole as the key intermediate.
Co-reporter:Wei Lin, Guo-Lan Dou, Ming-Hua Hu, Cheng-Pao Cao, Zhi-Bin Huang, and Da-Qing Shi
Organic Letters 2013 Volume 15(Issue 6) pp:1238-1241
Publication Date(Web):March 1, 2013
DOI:10.1021/ol400154j
A concise and efficient route to new and interesting heterohelicene-like molecules has been developed through the one-pot, cascade reductive coupling reaction of o-hydroxydiimines or o-nitrodiimines and triphosgene in the presence of TiCl4/Sm. Purification of the final products only required a single recrystallization leading to high purity. High diastereoselectivity was also achieved, and two structures of the final products were confirmed by X-ray diffraction analysis.
Co-reporter:Cheng-Pao Cao, Wei Lin, Ming-Hua Hu, Zhi-Bin Huang and Da-Qing Shi
Chemical Communications 2013 vol. 49(Issue 62) pp:6983-6985
Publication Date(Web):26 Jun 2013
DOI:10.1039/C3CC43489C
A series of new octahydrobenzo[b]indeno[1,2,3-de][1,8] naphthyridine and decahydropyrido[2,3,4-gh]phenanthridine derivatives were synthesized via a four-component domino reaction under microwave irradiation. This one-pot transformation, which involved multiple steps and did not require the use of a catalyst, constructed four new C–C bonds, two new C–N bonds, and three new rings, with efficient use of all reactants.
Co-reporter:Wei Lin, Ming-Hua Hu, Xian Feng, Cheng-Pao Cao, Zhi-Bin Huang, Da-Qing Shi
Tetrahedron 2013 69(32) pp: 6721-6726
Publication Date(Web):
DOI:10.1016/j.tet.2013.05.074
Co-reporter:Huiyuan Wang, Lili Li, Wei Lin, Pan Xu, Zhibin Huang, and Daqing Shi
Organic Letters 2012 Volume 14(Issue 17) pp:4598-4601
Publication Date(Web):August 24, 2012
DOI:10.1021/ol302058g
An efficient domino approach for the synthesis of novel pyrrolo[2,3,4-kl]acridin-1-one derivatives has been established. This reaction represents the first facile conversion of an isatin to a pyrrolo[2,3,4-kl]acridin-1-one via a C–N bond cleavage reaction without the need for a multistep reaction process.
Co-reporter:Dong-Jing Han;Shun-Jun Ji
Journal of Heterocyclic Chemistry 2011 Volume 48( Issue 6) pp:1393-1397
Publication Date(Web):
DOI:10.1002/jhet.666
Abstract
New crown ether carrying two fluorionophores of cis-dibenzothiazolyldibenzo-24-crown-8 was synthesized from cis-diformyldibenzo-24-crown-8 and 2-aminobenzenethiol. The binding behavior and the optical properties of the crown ether were examined through UV-visible spectroscopy and fluorescence spectroscopy. When complexed with Na+, K+, Rb+, and Cs+ ions, it led to intramolecular charge transfer and caused the changes of the fluorescence spectra. The protonation of the crown ether was also studied. With protonation using CF3COOH, the absorption bands and the fluorescence spectroscopy changed, the maximal fluorescence wavelengths red shifted and the fluorescence intensity with the maximum at 433 nm enhanced strongly. J. Heterocyclic Chem., (2011).
Co-reporter:Zhi-Bin HUANG;Sung-Hong KIM;Da-Qing SHI;Tai-Jong KANG;Seung-Hyun CHANG
Chinese Journal of Chemistry 2008 Volume 26( Issue 6) pp:1096-1100
Publication Date(Web):
DOI:10.1002/cjoc.200890194
Abstract
A new crown ether of 2,13-dibenzothiazol-2′-yldibenzo[b,k]-18-crown-6 was synthesized from 2,13-diformyl- dibenzo[b,k]-18-crown-6 with 2-aminothiophenol. The binding behavior and the optical properties of the crown ether were examined through UV-visible spectroscopy and fluorescence spectroscopy. When complexed with Na+, K+, Rb+ and Cs+ ions, it led to intramolecular charge transfer and caused the changes of the fluorescence spectra. The protonation of the crown ether was also studied.
Co-reporter:Cheng-Pao Cao, Wei Lin, Ming-Hua Hu, Zhi-Bin Huang and Da-Qing Shi
Chemical Communications 2013 - vol. 49(Issue 62) pp:NaN6985-6985
Publication Date(Web):2013/06/26
DOI:10.1039/C3CC43489C
A series of new octahydrobenzo[b]indeno[1,2,3-de][1,8] naphthyridine and decahydropyrido[2,3,4-gh]phenanthridine derivatives were synthesized via a four-component domino reaction under microwave irradiation. This one-pot transformation, which involved multiple steps and did not require the use of a catalyst, constructed four new C–C bonds, two new C–N bonds, and three new rings, with efficient use of all reactants.