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New 2‐methylisothiazolones
Author(s) -
Nádel Ágnes,
Pálinkás János
Publication year - 2000
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.5570370610
Subject(s) - chemistry , cystine , bromide , hydrobromide , acetic anhydride , amino acid , organic chemistry , acetic acid , sulfuryl chloride , medicinal chemistry , stereochemistry , biochemistry , enzyme , cysteine , catalysis
New N,N' ‐bis(alkoxycarbonyl)‐L‐cystine bis(methylamides) 4a, 4b and N,N' ‐bis(benzyloxycarbonyl)‐L‐cystine bis(methylamide) 4c have been synthesized by mixed anhydride method from the essential amino acid L‐cystine 1 in good yield. These cystine bis(methylamides) 4a,b,c have been cyclized with sulfuryl chloride. New 2‐methyl‐4‐amino‐3‐isothiazolone and 5‐chloro‐2‐methyl‐4‐amino‐3‐isothiazolone hydrobromide salts 7, 8 have been obtained by deacylation of 2‐methyl‐4‐(benzyloxycarbonyl)amino‐3‐isothiazolone 5c and 5‐chloro‐2‐methyl‐4‐(benzyloxycarbonyl)amino‐3‐isothiazolone 6c with hydrogen bromide in acetic acid. The microbicidal effect of the new 2‐methy]‐3‐isothiazolones 5a,b,c; 6a,b,c; 7 and 8 compounds obtained by the above method has been investigated.