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Síntesis selectiva de 1,2-dihidropiridinas sustituidas por N a partir de furanos por catálisis simultánea en tándem

Manuel R Fructos¹, Eleuterio Alvarez, M Mar Díaz-Requejo

¹Laboratorio de Catalisis Homogenea, Departamento de Quimica y Ciencia de los Materiales, Unidad Asociada al CSIC, Campus de El Carmen s/n, Universidad de Huelva, 21007-Huelva, Spain.

Journal of the American Chemical Society

|March 17, 2010

Resumen

Los investigadores desarrollaron un nuevo método para convertir los furanos sustituidos en 1,2-dihidropiridinas utilizando catalizadores de cobre o plata. Esta reacción de una sola olla involucra cuatro ciclos catalíticos, ofreciendo una nueva ruta sintética para valiosos compuestos heterocíclicos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los derivados de furanos son versátiles bloques de construcción en la síntesis orgánica.
El desarrollo de métodos catalíticos eficientes para la síntesis de compuestos heterocíclicos es crucial.

Objetivo del estudio:

Informar sobre una nueva transformación de los furanos en 1,2-dihidropiridinas.
Para dilucidar el mecanismo catalítico que involucra a los complejos metálicos.

Principales métodos:

Reacción de los furanos sustituidos por mono o dialquilo con los PhI (NT) 2.
Catálisis por complejos de cobre (Cu) y plata (Ag) con la fórmula general Tp(x) M.
Procedimiento de una sola olla que involucra cuatro ciclos catalíticos consecutivos.

Principales resultados:

Conversión exitosa de los furanos en 1,2-dihidropiridinas a temperatura ambiente.
Identificación de las etapas clave: aziridinación de furano, apertura de anillos, transiminación, reacción aza-Diels-Alder y eliminación de hidrógeno.
Demostrando el papel crucial del catalizador del complejo metálico.

Conclusiones:

Se ha establecido una nueva y eficiente ruta sintética de una sola olla para las 1,2-dihidropiridinas de los furanos.
La reacción procede a través de una compleja cascada de cuatro ciclos catalíticos.
Los complejos metálicos juegan un papel fundamental en la mediación de la transformación general.

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