The synthesis of n-substituted isothiazol-3(2h)-ones from nsubstituted 3-benzoylpropionamides

✍ Scribed by Stylianos Hamilakis; Demetrios Kontonassios; Athanase Tsolomitis

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 86 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390122

✦ Synopsis

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.