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Ring transformation of 5‐aroyl‐3(2 H )‐isothiazolones to 1,2,5‐oxathiazole and 1,2,3‐thiadiazole derivatives
Author(s) -
Tsolomitis A.,
Sandris C.
Publication year - 1984
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.5570210622
Subject(s) - chemistry , phenylhydrazine , hydroxylamine , hydrazine (antidepressant) , ring (chemistry) , medicinal chemistry , ketone , thiadiazoles , methylene , nucleophile , aryl , hydrazone , azetidine , stereochemistry , organic chemistry , alkyl , catalysis , chromatography
Reaction of 2‐substituted‐5‐aroyl‐3(2 H )‐isothiazolones 2 with hydroxylamine and phenylhydrazine was found to give ( N ‐substituted‐carboxamido)methylene derivatives of 1,2,5‐oxathiazole and 1,2,3‐thiadiazole, 5 and 7 , respectively. The formation of these heterocycles was ascribed to a mononuclear heterocyclic rear‐rangement of the initially formed ketone derivatives, oximes and hydrazones, through a nucleophilic attack of the = N‐OH and = N‐NH‐ groups on the SN bond of the isothiazolone ring. In a similar manner, reaction of isothiazolones 2 with hydrazine was found to give 4‐aryl‐5‐( N ‐substituted‐carboxamido)methyl‐1,2,3‐thiadiazoles 17 .