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An unusual labilization of a 4‐(trifluoromethyl)thiazole
Author(s) -
South Michael S.
Publication year - 1991
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.5570280430
Subject(s) - chemistry , trifluoromethyl , thiazole , diethylamine , triethylamine , medicinal chemistry , ring (chemistry) , thiazolidine , methanol , organic chemistry , alkyl
N ‐Chloro‐4‐(trifluoromethyl)‐5‐thiazolyl‐ N',N' ‐diethylurea 5 has been found to undergo a facile labilization of the trifluoromethyl group under mild conditions. The reaction relies on the assistance of the nitrogen substitution at the 4‐position of the thiazole ring. Treatment of 5 with triethylamine and either methanol or methanethiol replaced the trifluoromethyl group with a methyl ester or a trimethylorthothio ester respectively at room temperature. Combination of 5 with diethylamine led to an unusual thiazolidine with two exocyclic double bonds, 8 .