A novel bioactive compounds of 2-azetidinone derived from pyrazin dicarboxylic acid: synthesis and antmicrobial screening

Abstract

A series of novel 2-azetidinons entitled N, N’-bis[3-chloro-2-oxo-4-(substituted pyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide and N,N’-bis[3,3-dichloro-2-oxo-4-(substitutedpyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide have been synthesized from the relating newly Schiff bases by [2+2] cycloaddition reaction in good yields. Starting with pyrazine-2,3-dicarboxylic acid which was converted to the corresponding diester in absolute ethanol and glacial acetic acid as a catalyst. After that, the hydazinolysis of resulted diester with hydrazine hydrate afforded dicarbohydrazide which further treated with different substituted pyridine-2-carbaldehyde to give new Schiff bases. These new Schiff bases were reacted with chloroacetochloride and (or) dichloroacetochloride in presence of trimethylamine in DMF solvent under reflux and stirring to yield new derivatives of titled compounds. The structural assignments were estimated from their spectroscopic analysis such as IR,1H NMR, 13C NMR, and C, H, N elemental analysis. The newly prepared 2-azetidinones have been screened for their antimicrobial activity and some of them revealed excellent antibacterial and antifungal activities.