Reactivities of 4-Arylthio-2-azetidinones

Abstract

Reactivities of 3-methyl-4-arylthio-2-azetidinones (IIIa and IIIb) and their N-chlorosulfonyl derivatives (IIa and IIb) are discussed. Treatment of IIIa with hexamethylphosphoramide (HMPA) gave the acrylonitrile derivative (Va). The arylthio group of IIIa was easily oxidized with m-chloroperbenzoic aicd to afford the sulfoxide (VII), and further oxidation gave sulfone derivative (IX). Treatment of IIIa with iodine or bromine in methylene chloride gave the disulfide (VI) in high yield. Reaction of IIIa with 2-methylthio-2-thiazoline gave 6-methyl-5-oxo-5H-2, 3-dihydrothiazolo [3, 2-a] pyrimidine (XII) in 16% yield.