Synthesis and Characterization of Some Novel 4-Thiazolidinones and Isoxazolines Derived from Thiosemicarbazones

Abstract

A Novel compounds of 1,3-thiazolidine-4-ones and isoxazolines fused with thiazolidine ring have been synthesized from some thiosemicarbazones. The thiosemicarbazones were prepared by the reaction of thiosemicarbazide with diffrent aldehydes and ketones. A2-substituted-1,3-thiazolidine-4-oneswere synthesized by the reaction of thiosemicarbazones with chloroacetic acid in presence of anhydrous sodium acetate. The 4-thiazolidinones have a double bond at the position -5 of the 4-thiazolidinone ring. The double bond was inserted by the reaction of thiazolidinones with benzaldehyde in piperidine. Hydroxylamine hydrochloride was used to convert the later compounds to isoxazolines fused with thiazolidine ring. Furthermore, 4-thiazolidinones containing N-acetyl group were obtained by the reaction of 4-thiazolidinones with acetic anhydride. The structures of newly synthesized compounds were established on the basis of spectroscopy data.