Some new aspects in the chemistry of 4-alkylidene-Δ2-thiazolin-5-ones

Abstract

2-Phenyl-Δ²-thiazolin-5-one (6) was condensed with various ketones to give 4-alkylidene-2-phenyl-Δ²-thiazolin-5-one (2). Treatment of these compounds with acylating agents afforded 5-acyloxy-4-alkenyl-2-phenylthiazoles (8) and (9). Sodium borohydride and sodium borodeuteriide reduced the 4-alkylidenethiazolones at the exocyclic double bond to give the respective 4-alkyl-2-phenyl-Δ²-thiazolin-5-ones (10) and (11).