Tetrahedron

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

C Mukherjee, S Kamila, A De

Index: Mukherjee, Chandrani; Kamila, Sukanta; De, Asish Tetrahedron, 2003 , vol. 59, # 26 p. 4767 - 4774

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Citation Number: 29

Abstract

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 ...

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