A green approach to the production of 2-pyridone derivatives promoted by infrared irradiation

Fernando Hernández, Fabiola De la Cruz, Julio López, Eduardo Peña, Francisco Delgado, Yolanda Alcaraz, Juvencio Robles, Minerva Martínez-Alfaro, Miguel A. Vázquez

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6 Scopus citations

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.

Original languageEnglish
Pages (from-to)152-158
Number of pages7
JournalJournal of the Mexican Chemical Society
Volume58
Issue number2
StatePublished - 2014

Keywords

  • 2-pyridones
  • 4H-pyrans
  • Green approach
  • Infrared irradiation
  • Rearrangement

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