The Hantzsch Ester Production in a Water-based Biphasic Medium, Using Infrared Irradiation as the Activating Source
Raquel Gómez-Pliego,1,3 Roberto Osnaya,1,2 Isai Zamora,1 Benjamín Velasco-Bejarano,1 Gabriel Arroyo,1 Eduardo Ramírez-San Juan,2 José Trujillo,3 Francisco Delgado,2 René Miranda1*
1 Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Campo 1, Universidad Nacional Autónoma de México, Av. 1ro de Mayo s/n, Cuautitlán Izcalli, Estado de México, C. P. 54740. *e-mail: mirruv@yahoo.com.mx
2 Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación Carpio y Plan de Ayala, C. P. 11340 México, D. F.
3 Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón s/n Col. Santo Tomás, México, D.F., C. P. 11340.
]]>Recibido el 4 de junio de 2007
Aceptado el 14 de septiembre de 2007
Abstract
The reaction of a wide number of benzaldehydes (1a-n) with ethyl (2a) or methyl (2b) acetoacetate and aqueous ammonia (3) has been carried out in the absence of an organic solvent, and using for the first time infrared irradiation as the heating mode. Thus, under the green chemistry protocole, the corresponding mono-1,4-dihydropyridines (4a-j) and bis-1,4-dihydropyridines (4k-n) were obtained in good yields and short reaction times.
Key words: Hantzsch synthesis, benzaldehydes, 1,4-dihydropyridines, infrared irradiation, green chemistry.
Resumen
En este trabajo se presentan y discuten los resultados obtenidos de la reacción entre varios banzaldehídos (1a-n) con acetoacetato de etilo (2 a) o metilo (2b) e hidróxido de amonio (3); lo anterior mediante el protocolo de la química verde: ausencia de disolvente orgánico y empleando irradiación infrarroja como fuente de activación. De esta manera se obtuvieron las correspondientes mono-1,4-dihidropiridinas (4a-j) y bis-1,4-dihidropiridinas (4k-n) con buenos rendimientos y en tiempos cortos de reacción.
]]> Palabras clave: Síntesis de Hantzsch, benzaldehídos, 1,4-dihidropiridinas, radiación infrarroja, química verde.
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Acknowledgement
We appreciate the financial support of DGAPA-UNAM PAPIIT grant IN 213107; F. D. would like to acknowledge CONACyT (Grant 44038-Q) and CGPI/IPN (Grant 20050297) for financial support. Raquel Gómez acknowledges DGETI-SEP for scholarship support. F.D. is fellow of the EDI/IPN and COFAA/IPN programs.
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