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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 352–358 | Cite as

Catalyst-free three-component synthesis of new pyrrolidine derivatives via 1,3-dipolar cycloaddition

  • Yazmin Villarreal
  • Braulio Insuasty
  • Rodrigo Abonia
  • Alejandro Ortiz
  • Jairo QuirogaEmail author
Article
  • 22 Downloads

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 

Notes

The authors wish to thank Universidad del Valle, COLCIENCIAS and Science, Technology, and Innovation Fund-General Royalties System (FCTeI-SGR) under contract BPIN 2013000100007 for financial support. Braulio Insuasty and Jairo Quiroga dedicate this manuscript to the memory of Professor V. D. Orlov in gratitude for his valuable teaching and advising during completion of their doctoral studies under his tutorship in V. N. Karazin Kharkiv National University.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Yazmin Villarreal
    • 1
    • 2
  • Braulio Insuasty
    • 1
  • Rodrigo Abonia
    • 1
  • Alejandro Ortiz
    • 1
    • 2
  • Jairo Quiroga
    • 1
    Email author
  1. 1.Grupo de Investigación de Compuestos Heterocíclicos, Departamento de QuímicaUniversidad del ValleCaliColombia
  2. 2.Center for Bioinformatics and Photonics-CIBioFICaliColombia

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