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A synthesis of isothiazoles and pyrimidines via a vilsmeier‐haack reaction
Author(s) -
Crenshaw R. R.,
Partyka R. A.
Publication year - 1970
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.5570070419
Subject(s) - chemistry , sodium hydrosulfide , medicinal chemistry , iodine , organic chemistry , hydrogen sulfide , sulfur
A new synthesis of isothiazoles is reported which involves the reaction of Vilsmeier salts of N , N ‐dimethylamides with enamino nitriles, and treatment of the intermediates successively with sodium hydrosulfide and iodine. 4‐Isothiazolecarbonitriles prepared were: 3‐phenyl; 3,5‐dimethyl; 3,5‐diphenyl; 3‐methyl‐5‐phenyl; and 3‐phenyl‐5‐methyl. The 5‐phenylisothiazoles were obtained in low yields due to a side reaction involving the formation of pyrimidines. Pyrimidines encountered were 6‐chloro‐2,4‐diphenyl and 6‐chloro‐4‐methyl‐2‐phenylpyrimidines.