Synthesis of a New Class of Tris- and Bis(1,3,4-thiadiazol-2-amine) Methyl and Ethyl Tris- and Bis-2-(2-(2-benzoyl hydrazinyl)-4-oxothiazolidine) Acetate Derivatives

Abstract

Hydrazine, carbothioamide derivatives 2, 3, and 4 were synthesized by the condensation of 1, 3, 5-tri carbonyl tri chloride, Terephthaloyl dichloride, and 1, 4-dicarbonyl chloride with thiosemicarbazide in presence of pyridine as a solvent. The reaction of compounds 2, 3, and 4 with DMAD or DEAD led to the formation of 4-oxothiozolidine derivatives (4b–c), (3a-c), and (2c-d). The treatment of compounds 2, 3, and 4 with 1, 4′-diboromoacetophenone resulted in the formation of thiazole derivatives (2g, 3f, 4f). The treatment of compounds 2, 3, and 4 with sulfuric led to the formation of 4H-1,2,4-triazole-3-thiol derivatives (2f, 3d, and 4d). The cyclization of compounds 2, 3, and 4 in the presence of 2N NaOH resulted in the formation of compounds 2e-4e containing two or three [1,2,4]triazole rings which are linked to the benzene ring. These compounds are important and useful monomer for synthesis of various dendrimers.