Regioselective Synthesis of Furfuryl-Substituted 1,2,3-Triazoles by 1,3-Dipolar Cycloaddition of 5-(Azidomethyl)furfural to Methyl Alka-2,3-dienoates

Abstract

A procedure has been proposed for the regioselective synthesis of new 1,2,3-triazole derivatives from methyl alka-2,3-dienoates. The effect of substituents in the initial reactants on the regio- and stereo­selectivity of the reaction has been studied, and the synthesized compounds have been characterized by physicochemical methods. Regioselective 1,3-dipolar cycloaddition of 5-(azidomethyl)furfural [prepared from 5-(chloromethyl)furfural] to alka-2,3-dienoates containing a cyclic imide fragment in toluene afforded substituted 1,2,3-triazoles with maximum remoteness of the furfuryl and ester groups from each other, which minimizes steric repulsion.