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Síntesis de indoles a través de la formación cíclica de 2,3-Dizincioindoles y el atrapamiento electrófilo

Laurean Ilies¹, Mayuko Isomura¹, Shin-Ichi Yamauchi¹

¹Department of Chemistry and Molecular Technology Innovation Chair, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|December 23, 2016

Resumen

Una nueva reacción de ciclización transforma la 2-etinilanilina protegida por N en un intermediario de dizincioindol. Este intermediario permite la funcionalización selectiva, lo que permite una síntesis eficiente de valiosos derivados de la indenoindolona y el benzodipirrol.

Área de la Ciencia:

Química orgánica
Química organometálica

Sus antecedentes:

Los derivados de la 2-etinilanilina son precursores de importantes compuestos heterocíclicos.
Las reacciones de metalización son clave para la funcionalidad de las moléculas orgánicas.

Objetivo del estudio:

Desarrollar un nuevo método para la síntesis de indolos 2,3-disubstituidos.
Para explorar la reactividad de un intermediario dizincioindole.

Principales métodos:

Zincado de la 2-etinilanilina protegida con N a 120 °C.
Funcionalización selectiva del intermediario dizincioindole con electrófilos.
Detección de la regioselectividad por catalizadores y electrófilos.

Principales resultados:

Ciclización suave para formar un intermediario de 2,3-dizincioindole.
Funcionalización selectiva inter e intramolecular en las posiciones C2 o C3.
Síntesis rápida de los derivados de la indenoindolona y el benzodipirrol.

Conclusiones:

La estrategia de zincación y ciclización desarrollada proporciona un acceso eficiente a los indoles funcionalizados.
Este método ofrece una vía versátil para los compuestos relevantes para la química medicinal y la ciencia de los materiales.

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