Synthesis and Characterization of Some New Derivatives of 5-Arylidene-2,4-thiazolidinediones

Abstract

Keeping in view the immense biological and pharmacological importance of 5-arylidene-2,4-thiazolidinediones, some new derivatives were synthesized. Initially, 5-arylidene derivatives of 2,4-thiazolidinedione were synthesized. The syntheses were achieved by the condensation of aromatic aldehydes with 2,4-thiazolidinediones. The 3-substituted 5-arylidene-2,4-thiazolidinediones were in turn synthesized by thiocarbohydrazides and benzohydrazides. The thiocarbohydrazide precursor was prepared from carbon disulfide and hydrazine hydrate, that led to the synthesis of 3-substituted 1,2,4-triazole derivatives of 5-arylidene-2,4-thiazolidinediones. Benzohydrazide precursor was synthesized by the reaction of methyl benzoate with hydrazine hydrate, and converted into 3-substituted 1,3,4-oxadiazole derivatives of 5-arylidene-2,4-thiazolidinediones on treatment with acid hydrazides in presence of dehydrating agents. The structures of newly synthesized compounds were established by using available spectroscopic techniques. Syntheses were carried out by stepwise method successfully. For the synthesis of 5-arylidene derivatives, various conditions (temperatures, solvents and bases) were applied to increase the yield of products and lower the reaction times.