Application of directed metalation in synthesis.: Part 4:: Expedient synthesis of substituted benzo[b]thiophene and naphthothiophene

被引：35

作者：

Mukherjee, C ^{[1
]}

Kamila, S ^{[1
]}

De, A ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 26期

关键词：

benzo[b]thiophene; directed metalation; thioindoxyl; naphthothiophene; intramolecular cyclisation;

D O I：

10.1016/S0040-4020(03)00710-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, simple and inexpensive synthesis of several diversely substituted benzo[b]thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho- to the amide function of readily available N,N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo[b]thiophene or napthothiophene. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4767 / 4774

页数：8

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