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Synthesis and reactions of the thioamide derivatives of methyl vinyl ketone

✍ Scribed by Łukasz Groś; Aneta Wesołowska; Sławomir Westerlich; Tadeusz Jagodziński

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
645 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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The reaction of isothiocyanates with in situ generated carbanions of α,β‐unsaturated ketones yielded α,β‐unsaturated keto thioamides which in the reaction with acids or bases cyclized to give 2,6‐disubstituted thiopyran‐4‐ones and in the reaction with α‐bromoesters gave thiazolidin‐4‐one derivatives. The thiopyran‐4‐ones reacted with α,β‐unsaturated aldehydes to yield tetrahydrothiopyran[2,3‐b]pyridin‐4‐ones, while thioanilides were formed in the reaction with phenyl isothiocyanate.

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