Synthesis of (4-Chlorophenyl)-(1-oxo-1λ4-benzo[b]thien-2-yl)methanone and study of its reactivity towards sulfur- and oxygen-containing nucleophiles.

被引：14

作者：

Pouzet, P ^{[1
]}

Erdelmeier, I ^{[1
]}

Dansette, PM ^{[1
]}

Mansuy, D ^{[1
]}

机构：

[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, URA 400, F-75270 Paris 06, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

benzothiophenes; oxidation; sulfoxides; Michael reactions;

D O I：

10.1016/S0040-4020(98)00929-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(4-Chlorophenyl)-(1-oxo-1 lambda(4)-benzo[b]thien-2-yl)methanone 2a was synthesized by oxidation of the corresponding benzo[b]thiophene derivative 2 with the oxidative system H2O2/TFA. This benzo[b]thiophene sulfoxide undergoes Michael-type nucleophilic addition of sulfur- and oxygen-containing nucleophiles either under basic conditions leading to 2,3-dihydro-3-substituted-benzo[b]thiophene 1-oxides or in acidic media leading then to rearomatized 3-substituted-benzo[b]thiophenes. This method provides an easy two-step functionalization of 2-acyl-benzo[b]thiophene derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14811 / 14824

页数：14

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