CATALYST-FREE THREE-COMPONENT SYNTHESIS OF NEW PYRROLIDINE DERIVATIVES via 1,3-DIPOLAR CYCLOADDITION

Abstract

Differently substituted pyrrolidine derivatives have been prepared by a three-component reaction of heterocyclic aldehydes, amino acid methyl or ethyl esters, and trans-1,2-dibenzoylethylene in toluene under catalyst-free conditions. This simple one-step procedure allows to obtain the desired 3,4-dibenzoyl-5-hetarylpyrrolidines in high yields ensuring high diastereoselectivity. Given the fact that the fundamental stage of the proposed reaction mechanism is based on 1,3-dipolar cycloaddition, DFT and TDDFT quantum-chemical calculations have been used for better understanding and characterization of geometry and electronic structure of the reaction intermediates and products.