Synthesis, Characterization, Antifungal and Antibacterial Activities of Novel Amide Derivatives of 1,3-Dioxolane

Abstract

L-Tartaric acid which is chiral compound and commercially available, was converted into 1,3-dioxolane. In the synthetic sequence, 1,3-dioxolane was first formed via protection and partial hydrolysis of L-tartaric acid. Treatment with altered substituted aromatic amines, 1,3-dioxolane gave the desired amides i.e. ethyl 2,2-dimethyl-5-(phenylcarbamoyl)-1,3-dioxolane-4-carboxylate 3a, 2-(4-(ethoxycarbonyl)-2,2-dimethyl-1,3-dioxolane-5-carboxamido)benzoic acid 3b, ethyl 5-(4-iodophenylcarbamoyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 3c, ethyl 5-(2-chlorophenylcarbamoyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 3d and ethyl 5-(2,4-dichlorophenylcarbamoyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 3e. These chiral derivatives were purified through column chromatographic technique and characterized by different spectroscopic techniques i.e IR, 1H NMR, 13C NMR and EIMS. The antimicrobial activities of these compounds were determined at different concentrations against different strains of bacteria and fungi.