Premium
Synthesis and reactions of the thioamide derivatives of methyl vinyl ketone
Author(s) -
Groś Łukasz,
Wesołowska Aneta,
Westerlich Sławomir,
Jagodziński Tadeusz
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440126
Subject(s) - chemistry , thioamide , thiopyran , methyl vinyl ketone , carbanion , yield (engineering) , ketone , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
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.