Design and Synthesis of Novel Bis Thiazolo[4,5-c]Isoxazolines Bearing 1,2,4-triazole Ring Derived From the Related 4-thiazolidinons as Antimicrobial Agents

Abstract

Design and synthesis of novel poly heterocycles together using same heterocyclic compound is the main task of the present paper. The target compounds entitled 4,4’-[benzene-1,4-diylbis[ethylidenehydrazine-2-ylidene]bis[4-[3,5-di(5-substitutedpyridin-2-yl)-3,3a-dihydro[1,3]thiazolo[4,5-c][1,2]oxazol-6(5H)-yl]-4H-3-yl-1,2,4-triazole-3-thiol] have been synthesized starting from the reaction of 1,4-diacetylphenyl and carbohydrazide to give Schiff base derivatives then 1,2,4- triazole derivatives from the reaction with CS₂ and an excess of hydrazine hydrate. The same applies for the condensing of these newly heterocyclic amines with different pyridine-2-carbaldehydes, which resulted in the synthesis of some new Schiff bases, which were then cyclized to develop new thiazolidinones by thioglycolic acid. Additionally, by fusing thiazolidinones with various pyridine-2-carbaldehydes, a novel chalcone was formed. To produce the desired fused isoxazolines, the later compounds underwent cyclization with hydroxylamine hydrochloride and potassium hydroxide. From the examination of the (CHN), FTIR, ¹H NMR, and ¹³C NMR spectra, the structural identities of all recently synthesized compounds were determined. The newly synthesized chemicals were also successfully tested as an antibacterial agent.