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

Yazmín Villareal, Braulio Insuasty, Rodrigo Abonia, Alejandro Ortiz, Jairo Quiroga
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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.


Keywords


amino acid ester; azometine ylide; 1,2-dibenzoylethylene; heterocyclic aldehyde; pyrrolidine; multicomponent reaction

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