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The synthesis of n ‐substituted isothiazol‐3(2 h )‐ones from n substituted 3‐benzoylpropionamides
Author(s) -
Hamilakis Stylianos,
Kontonassios Demetrios,
Tsolomitis Athanase
Publication year - 2002
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.5570390122
Subject(s) - chemistry , substituent , thionyl chloride , medicinal chemistry , alkyl , group (periodic table) , chloride , stereochemistry , organic chemistry
Abstract N ‐Substituted isothiazol‐3(2 H )‐ones can be easily prepared from N ‐substituted 3‐benzoylpropi‐onamides in two experimentally simple steps, in satisfactory overall yields. Reaction of the amides with excess thionyl chloride results in the formation of N ‐substituted 5‐benzoylisothiazol‐3(2 H )‐ones, which are readily debenzoylated with alkali to the corresponding N ‐substituted isothiazol‐3(2 H )‐ones. This method has now been successfully applied to the synthesis of isothiazolones N ‐substituted with a bulky alkyl group, such as the tert ‐butyl group, and with a phenyl group bearing either a strong electron‐withdrawing substituent, such as the 3‐nitrophenyl and 4‐nitrophenyl group, or an electron‐releasing substituent, such as the 4‐methylphenyl and 4‐methoxyphenyl group.