Synthesis of some new derivatives of triazole using ortho-carboxybenzaldehyde as a synthone

Abstract EN

In this work, the 1,2,4-triazole ring was prepared by introducing the starting material ortho-carboxybenzaldehyde (1) in the usual esterification reaction, in ethanol as a solvent and in the presence of concentrated sulfuric acid to give ethyl-2-formylbenzoate (2), then introducing the resulting ester in a condensation reaction with thiosemberazide in the presence of ethanol as a solvent to afforded 2-(2-formylbenzoyl)hydrazine-1-carbothioamide (3), which on cyclisation using a solution of sodium hydroxide to obtain the 1,2,4-triazole compound (4), which on treatment with different primary aromatic amines to obtain Schiff bases (5a-e) the prepared Schiff bases were introduced into a reaction with chloroacetyl chloride in the presence of triethylamine as an auxiliary base for the reaction to prepare the tetracyclic azitidinone compounds (beta-lactams) (6a-e) along with the triazole ring in the same compound.

Finally, these prepared compounds were characterized by physical and spectroscopic measurements such as melting point, thin layer chromatography (m.p., TLC) infrared spectroscopic measurements FT-IR, and nuclear magnetic resonance spectra of some compounds1H-NMR.

Keywords: ortho-carboxybenzaldehyde,