Solvent-free synthesis of functionalized pyridine derivatives using Wells-Dawson heteropolyacid as catalyst |
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Authors: | Laura M. SanchezÁ ngel G. Sathicq,Jorge L. JiosGraciela T. Baronetti,Horacio J. ThomasGustavo P. Romanelli |
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Affiliation: | a Centro de Investigación y Desarrollo en Ciencias Aplicadas ‘Dr. J.J. Ronco’ (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CCT-CONICET, Calles 47 No 257, B1900AJK La Plata, Argentina b LaSeISiC, Departamento de Química, Facultad de Ciencias Exactas, UNLP-CICPBA, La Plata, Argentina c Departamento de Ingeniería Química, Facultad de Ingeniería, Universidad de Buenos Aires, Ciudad Universitaria, C1428BG Buenos Aires, Argentina d Planta Piloto Multipropósito PlaPiMu, UNLP-CICPBA, Camino Centenario y 508, CP1987, Manuel B, Gonnet, Argentina |
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Abstract: | Wells-Dawson heteropolyacids (H6P2W18O62·24H2O) were used as catalysts in the Hantzsch-like multicomponent condensation reaction with 3-formylchromones as aldehyde component, a β-ketoester and ammonium acetate, under solvent-free conditions at 80 °C. Although the desired products were obtained, functionalized pyridines were the main reaction product and became the alternative route to dihydropyridine ring formation. Based on the proposed mechanisms for the formation of each of the obtained products, the multicomponent reaction was modified to afford only the functionalized pyridines (60-99%). Our procedure represents a clean alternative for the synthesis of several highly functionalized pyridines. |
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Keywords: | Multicomponent reaction 3-Formylchromones Solvent-free organic synthesis Wells-Dawson heteropolyacid Functionalized pyridines |
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