Reaction of thioglycolate with alpha-fluoro-beta-(phenylthio)enones (or -enals): Synthesis of substituted alpha-carboxy-gamma-fluorothiophenes

被引：11

作者：

Andres, DF ^{[1
]}

Laurent, EG ^{[1
]}

Marquet, BS ^{[1
]}

机构：

[1] UNIV LYON 1, LAB CHIM ORGAN 3, CNRS, F-69622 VILLEURBANNE, FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(96)02509-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic method to substituted alpha-carboxy-gamma-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and alpha-fluoro-beta-(phenylthio)enones (or -enals) 1F, in DMSO (70 degrees C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-alpha-fluoro-beta-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of alpha-fluoro-beta-(dithianyl)butanone. (C) 1997, Elsevier Science Ltd.

引用

页码：1049 / 1052

页数：4

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