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

Авторы

  • Yazmín Villareal Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali Center for Bioinformatics and Photonics-CIBioFI, Calle 13 No. 100-00, Edificio 320, No. 1069, Cali
  • Braulio Insuasty Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali
  • Rodrigo Abonia Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali
  • Alejandro Ortiz Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali Center for Bioinformatics and Photonics-CIBioFI, Calle 13 No. 100-00, Edificio 320, No. 1069, Cali
  • Jairo Quiroga Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, A. A. 25360, Cali

DOI:

https://doi.org/10.1007/4973

Ключевые слова:

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

Аннотация

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.

Опубликован

2019-05-22