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La ruta de Neber hacia los indolos sustituidos

Douglass F Taber¹, Weiwei Tian

¹Department of Chemistry and Biochemistry, University of Delaware, Newark, 19716, USA. taberdf@udel.edu

Journal of the American Chemical Society

|January 26, 2006

Resumen

Nuevos métodos convierten las oximas de cetona alfa-arilo en azirinas, que luego se reorganizan en indoles. Esto ofrece una alternativa versátil a la síntesis de indol de Fischer para crear compuestos de indol.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.

Sus antecedentes:

Los indoles son compuestos heterocíclicos cruciales que se encuentran en productos farmacéuticos y productos naturales.
Las rutas sintéticas existentes, como la síntesis de indol de Fischer, tienen limitaciones.

Objetivo del estudio:

Desarrollar nuevos procedimientos complementarios para la síntesis de indoles.
Establecer una vía versátil para los derivados de indol de las oximas de cetona alfa-arilo.

Principales métodos:

Conversión de oximas de cetonas alfa-arilo en azirinas mediante dos procedimientos distintos.
Reorganización térmica de las azirinas sintetizadas para formar indoles.

Principales resultados:

Desarrollo exitoso de dos métodos complementarios para la formación de azirina.
Suave reordenamiento térmico de las azirinas a los productos indólicos deseados.
Demostración de una vía sintética versátil para los indoles.

Conclusiones:

Los procedimientos desarrollados proporcionan una valiosa alternativa para la síntesis de indol.
Este método complementa la ya establecida síntesis de indol de Fischer.
Ofrece una nueva vía para acceder a diversas estructuras indole.

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