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Original Articles

A Simple Route to Benzo[b]thiophenes: Sulfanylation–Acylation of C─H Acids with 2-(Chlorosulfanyl)benzoyl Chloride

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Pages 1115-1123 | Received 14 Nov 2007, Accepted 24 Feb 2008, Published online: 28 Apr 2009
 

Abstract

A convenient procedure for the preparation of 2,2-disubstituted benzo[b]thiophen3(2H)-ones and 2-substituted 3-hydroxybenzo[b]thiophenes from β-diketones, β-keto- and β-cyanoesters, and β-cyanoketones, diethyl malonate, malonitrile, and anthrone has been developed. The tandem sulfanylation–acylation of these C─H acids resulting in the formation of a thiophene ring occurs upon treatment with 2-(chlorosulfanyl)benzoyl chloride in the presence of triethylamine.

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

The authors would like to express their thanks to Ministry of Science and Information for financial support (Grant N204022 31/0458).

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