Synthesis of triazoles from epoxides

Abstract

This project is aimed the synthesis of racemic and enantiopure triazoles from epoxides. The synthesis of beta-azido-alcohols is performed by conventional heating and / or microwave irradiation. The synthesis of beta-azido-alcohols and beta-azido-acetates by biocatalysis is obtained via hydrolysis reaction catalyzed by lipase from Candida antarctica (CALB). Initially, it is obtained the corresponding (±)-beta-azido- alcohol by opening the epoxide in aqueous medium in the presence of sodium azide. The (±)-beta-azido-alcohol is esterified with acetic anhydride and pyridine, yielding the (±)-beta-azido-acetate, which is subsequently subjected to enzymatic hydrolysis reaction by CALB. The enantiomerically pure and / or enriched products, after purification by column chromatography, will undergo cyclization to yield the triazoles.(AU)