A Green Approach to the Production of 2-pyridone Derivatives Promoted by Infrared Irradiation

Authors

  • Fernando Hernández Universidad de Guanajuato
  • Fabiola De la Cruz Universidad de Guanajuato
  • Julio López Universidad de Guanajuato
  • Eduardo Peña Universidad de Guanajuato
  • Francisco Delgado Escuela Nacional de Ciencias Biológicas-IPN
  • Yolanda Alcaraz Universidad de Guanajuato
  • Juvencio Robles Universidad de Guanajuato
  • Minerva Martínez-Alfaro Universidad de Guanajuato
  • Miguel A. Vázquez Universidad de Guanajuato

DOI:

https://doi.org/10.29356/jmcs.v58i2.171

Keywords:

4H-pyrans, rearrangement, 2-pyridones, infrared irradiation, green approach

Abstract

An alternative is presented for promoting a reaction with infrared irradiation to obtain different 4-aryl-3-cyano-5-ethoxycarbonyl-6-methyl-2-pyridone derivatives 9a-k. The process was carried out with a green approach from the corresponding 4H-pyrans, using mild reaction conditions and infrared irradiation as the energy source. In the first stage, the reaction produced 1,2,3,4-tetrahydropyridin-2-one derivatives 8a-k, followed by an oxidative step to afford the target molecules in good yields. The structure of products 9a-k was confirmed by FT-IR, 1H NMR and 13C NMR spectroscopic techniques and X-ray diffraction. It was found that the efficiency of the reaction depends on the catalyst and the solvent, as well as on the aldehyde substituents.

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Author Biographies

Fernando Hernández, Universidad de Guanajuato

Departamento de Química

Fabiola De la Cruz, Universidad de Guanajuato

Departamento de Química

Julio López, Universidad de Guanajuato

Departamento de Química

Eduardo Peña, Universidad de Guanajuato

Departamento de Química

Francisco Delgado, Escuela Nacional de Ciencias Biológicas-IPN

Departamento de Química Orgánica

Yolanda Alcaraz, Universidad de Guanajuato

Departamento de Farmacia

Juvencio Robles, Universidad de Guanajuato

Departamento de Farmacia

Minerva Martínez-Alfaro, Universidad de Guanajuato

Departamento de Farmacia

Miguel A. Vázquez, Universidad de Guanajuato

Departamento de Química

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Published

2017-10-12

Issue

Section

Regular Articles

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