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Cicloadición oxidativa catalizada por el rodio de benzamidas y alquinas a través de la activación C-H/N-H

Todd K Hyster¹, Tomislav Rovis

¹Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

Journal of the American Chemical Society

|July 29, 2010

Resumen

Una nueva reacción catalizada por Rh (III) permite la síntesis de isoquinolonas a partir de benzamidas y alquinas. Esta cicloadición oxidativa es altamente tolerante a los grupos funcionales y regioselectiva, ofreciendo rutas versátiles a valiosos andamios químicos.

Área de la Ciencia:

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

Sus antecedentes:

Las benzamidas y las alquinas son bloques de construcción orgánicos comunes.
El acceso a andamios de isoquinolona sustituidos es importante para la química medicinal.
Las cicloadiciones oxidativas ofrecen vías eficientes para la síntesis de heterociclos.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para la síntesis de isoquinolonas.
Para investigar el mecanismo y el alcance de la reacción desarrollada.
Explorar la utilidad de los compuestos sintetizados en la química medicinal.

Principales métodos:

Reacción de cicloadición oxidativa catalizada por Rh (III).
El cobre utilizado (II) oxidantes. oxidantes.
Mecanismo de reacción investigado a través de experimentos de competencia.

Principales resultados:

Con éxito sintetizó isoquinolonas de las benzamidas y las alquinas.
Se obtienen buenos rendimientos y una alta tolerancia al grupo funcional (haluros, éteres silílicos, aldehídos).
Se ha demostrado una excelente regioselectividad con alcinas asimétricas y carboxamidas de heteroarilo toleradas.

Conclusiones:

El sistema catalítico Rh (III) desarrollado proporciona una ruta eficiente a las isoquinolonas sustituidas.
El mecanismo de reacción implica la metalización de N-H y la activación de C-H orto.
La metodología ofrece acceso a nuevos andamios relevantes para el descubrimiento de fármacos.

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