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The formation of 2,3‐disubstituted thiazolidin‐4‐ones from s‐α'‐aminomercaptoacetic acid derivatives
Author(s) -
Tierney John
Publication year - 1989
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.5570260419
Subject(s) - chemistry , nitrobenzene , thioglycolic acid , toluene , carbon tetrachloride , kinetics , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics
Variously substituted N ‐benzylidineanilines rapidly react with thioglycolic acid to generate S‐α'‐aminomercaptoacetic acid derivatives. The latter subsequently cyclize to the corresponding 2,3‐diarylthiazolidin‐4‐ones. Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.