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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X


HERNANDEZ, Fernando et al. A Green Approach to the Production of 2-pyridone Derivatives Promoted by Infrared Irradiation. J. Mex. Chem. Soc [online]. 2014, vol.58, n.2, pp.152-158. ISSN 1870-249X.

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.

Keywords : 4H-pyrans; rearrangement; 2-pyridones; infrared irradiation; green approach.

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