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Las cascadas de anulación del indole redox-neutral de la anulación del indole.

Michael C Haibach¹, Indubhusan Deb, Chandra Kanta De

¹Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.

Journal of the American Chemical Society

|February 2, 2011

Resumen

Los aminobenzaldehídos y los indoles experimentan una nueva reacción en cascada, formando azepinoindoles policíclicos. Este proceso catalizado por ácido implica la condensación, el desplazamiento del hidruro y el cierre del anillo en un solo paso.

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Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Química Medicinal Química medicinal es el campo de la química medicinal.

Sus antecedentes:

Los derivados del indole son frecuentes en productos farmacéuticos y productos naturales.
La síntesis eficiente de andamios policíclicos complejos sigue siendo un desafío.

Objetivo del estudio:

Desarrollar una ruta sintética novedosa y eficiente para las azepinoindolas policíclicas.
Para explorar una nueva reacción en cascada que involucra aminobenzaldehídos e indoles.

Principales métodos:

Reacción catalizada por ácido de aminobenzaldehídos sustituidos con varios indolos.
Caracterización de los productos de reacción mediante espectroscopia de RMN, espectrometría de masas y cristalografía de rayos X.

Principales resultados:

Se descubrió una reacción en cascada sin precedentes entre aminobenzaldehídos e indoles.
La reacción se lleva a cabo a través de un mecanismo de condensación, desplazamiento de 1,5-hidruro y cierre de anillo.
Los azepinoindoles policíclicos fueron sintetizados en buenos a excelentes rendimientos en un solo paso.

Conclusiones:

Se ha establecido una nueva y eficiente síntesis de un solo paso para los azepinoindoles policíclicos.
La reacción en cascada desarrollada ofrece una herramienta valiosa para acceder a complejos heterociclos que contienen indol.
Esta metodología tiene potencial para la síntesis de nuevos agentes farmacéuticos.