One pot synthesis of tetrasubstituted thiophenes: [3+2] annulation strategy

被引：14

作者：

Sahu, Satya Narayan ^{[1
]}

Gupta, Maneesh Kumar ^{[1
]}

Singh, Surjeet ^{[1
]}

Yadav, Pratik ^{[1
]}

Panwar, Rahul ^{[1
]}

Kumar, Abhinav ^{[2
]}

Ram, Vishnu Ji ^{[2
]}

Kumar, Brijesh ^{[3
]}

Pratap, Ramendra ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Delhi 110007, India

[2] Univ Lucknow, Dept Chem, Lucknow 226007, Uttar Pradesh, India

[3] Cent Drug Res Inst, Div SAIF, Lucknow 226001, Uttar Pradesh, India

来源：

RSC ADVANCES | 2015年 / 5卷 / 46期

关键词：

FIELD-EFFECT TRANSISTORS; BIOLOGICAL-ACTIVITY; DERIVATIVES; SEMICONDUCTORS; OLIGOTHIOPHENES; SUBSTITUENT; INHIBITORS; NITRILEN; RECEPTOR; DESIGN;

D O I：

10.1039/c5ra01290b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple, efficient and economical synthesis of dimethyl 3-amino-5-(2-oxo-2-arylethyl)thiophene-2,4-dicarboxylates has been reported by ring opening of methyl 3-amino-6-aryl-4-oxo-4H-thieno[3,2-c]-pyran-2-carboxylates by alkoxide ions. Pyranothiophenes have been obtained by the reaction of methyl thioglycolate and 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles in the presence of triethylamine. A one-pot multicomponent protocol for the synthesis of tetrasubstituted thiophenes has been developed by reaction of 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles and methyl thioglycolate in the presence of sodium methoxide in excellent yields. The structure of the isolated compound was confirmed by single crystal X-ray diffraction and spectroscopic studies.

引用

页码：36979 / 36986

页数：8

共 50 条

[21] Silver-Catalyzed Coupling of Two Csp3-H Groups and One-Pot Synthesis of Tetrasubstituted Furans, Thiophenes, and Pyrroles
Mao, Shuai
Zhu, Xue-Qing
Gao, Ya-Ru
Guo, Dong-Dong
Wang, Yong-Qiang
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) : 11335 - 11339
[22] [3+2]-ANNULATION USING ALLYLIDENE(TRIPHENYL)PHOSPHORANES - A ONE-STEP SYNTHESIS OF CYCLOPENTADIENES
HATANAKA, M
HIMEDA, Y
UEDA, I
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19): : 2269 - 2274
[23] Synthesis of tetrasubstituted thiophenes via a [3+2] cascade cyclization reaction of pyridinium 1,4-zwitterionic thiolates and activated allenes
Zhai, Shengxian
Zhang, Xinping
Cheng, Bin
Li, Hui
Li, Yuntong
He, Yixuan
Li, Yun
Wang, Taimin
Zhai, Hongbin
CHEMICAL COMMUNICATIONS, 2020, 56 (20) : 3085 - 3088
[24] Electrooxidative [3+2] annulation of amidines with alkenes for the synthesis of spiroimidazolines
Zhang, Sai
Xu, Gaochen
Yan, Huan
Wu, Qinghuan
Meng, Jingjing
Duan, Jindian
Guo, Kai
CHINESE CHEMICAL LETTERS, 2022, 33 (12) : 5128 - 5131
[25] Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines
de Nanteuil, Florian
Waser, Jerome
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12075 - 12079
[26] Synthesis of (Carbo) nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes
Racine, Sophie
de Nanteuil, Florian
Serrano, Eloisa
Waser, Jerome
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) : 8484 - 8487
[27] [3+2] Annulation of allylidenetriphenylphosphorane with 1,2-diacylethylenes and 1,2-diacylacetylenes: A one-step synthesis of tri- and tetrasubstituted cyclopentadienes and fulvenes
Himeda, Y
Yamataka, H
Ueda, I
Hatanaka, M
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19): : 6529 - 6538
[28] Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3+2)-Annulation
Goodman, C. Guy
Walker, Morgan M.
Johnson, Jeffrey S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) : 122 - 125
[29] Synthesis of Norbornane-Bridged Diporphyrins via Palladium-Catalyzed [3+2] Annulation Strategy
Mizumura, Masatoshi
Shinokubo, Hiroshi
Osuka, Atsuhiro
SYNTHESIS-STUTTGART, 2009, (01): : 59 - 61
[30] A TOTAL SYNTHESIS OF PENTALENOLACTONE-E METHYL-ESTER VIA A [3+2] ANNULATION STRATEGY
MARINO, JP
SILVEIRA, C
COMASSETO, J
PETRAGNANI, N
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18): : 4139 - 4140

← 1 2 3 4 5 →