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

[31] One-pot synthesis of substituted 2-aminobenzo[b]thiophenes
Solovyev, Andrey Y.
Androsov, Dmitry A.
Neckers, Douglas C.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08): : 3122 - 3124
[32] A [3+2] ANNULATION PROCEDURE FOR METHYLENECYCLOPENTANES
KNAPP, S
OCONNOR, U
MOBILIO, D
TETRAHEDRON LETTERS, 1980, 21 (47) : 4557 - 4560
[33] [3+2] Annulation of Vinyl Azides with Aldehydes for the Synthesis of 3-Oxazolines via the [CO plus CCN] Strategy
Luo, Chun-Mei
Yang, Ming-Qi
Yang, Dong-Qing
Wu, Zhong-Qi
Zhou, Yu
Tian, Wen-Chan
Zhang, Jianfeng
Li, Qiang
Deng, Chao
Wei, Wen-Ting
ORGANIC LETTERS, 2024, 26 (32) : 6859 - 6865
[34] Facile Synthesis of Dispiroheterocycles through One-Pot [3+2] Cycloaddition, and Their Antiviral Activity
Zhang, Min
Yang, Wenbo
Li, Kailu
Sun, Ke
Ding, Jianfen
Yang, Liuqing
Zhu, Chunyin
SYNTHESIS-STUTTGART, 2019, 51 (20): : 3847 - 3858
[35] Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3+2] annulation and their in vitro evaluation as antibacterial agents
Balachandra, Biguvu
Shanmugam, Sivakumar
Muneeswaran, Thillaichidambaram
Ramakritinan, Muthiah
RSC ADVANCES, 2015, 5 (79) : 64781 - 64789
[36] One-pot double [3+2] cycloaddition for diastereoselective synthesis of tetracyclic pyrrolidine compounds
Lu, Qing
Song, Gonghua
Jasinski, Jerry P.
Keeley, Amanda C.
Zhang, Wei
GREEN CHEMISTRY, 2012, 14 (11) : 3010 - 3012
[37] New, diastereoselective one-pot synthesis of tetrasubstituted hydantoins
Alizadeh, Abdolah
Masrouri, Hassan
HELVETICA CHIMICA ACTA, 2006, 89 (06) : 1187 - 1193
[38] One-Pot Synthesis of Polysubstituted Spirofluorene-Indene via Ru(II)-Catalyzed [3+2] Annulation and Intramolecular Friedel-Crafts Cyclization
Zhu, Yu-Qin
Dong, Lin
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 9973 - 9979
[39] Synthesis of bicyclo[3.1.0]hexanes by (3+2) annulation of cyclopropenes with aminocyclopropanes
Muriel, Bastian
Gagnebin, Alec
Waser, Jerome
CHEMICAL SCIENCE, 2019, 10 (46) : 10716 - 10722
[40] Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles
Hanhan, Nadine V.
Ball-Jones, Nicolas R.
Tran, Ngon T.
Franz, Annaliese K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) : 989 - 992

← 1 2 3 4 5 →