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[4 + 2] cicloadiciones de iones N-alquenil ininio: heterociclos estructuralmente complejos de una secuencia de

Nihar Sarkar¹, Abhisek Banerjee, Scott G Nelson

¹University of Pittsburgh Center for Chemical Methodologies and Library Development, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Journal of the American Chemical Society

|June 26, 2008

Resumen

Este estudio introduce una nueva reacción de tres componentes utilizando iones de N-alkenil ininio para sintetizar diversos derivados de la piperidina. El método ofrece una ruta versátil para estructuras complejas de piperidina a través de la cicloadición y la adición nucleofílica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.
Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.

Sus antecedentes:

Los derivados de la piperidina son frecuentes en productos farmacéuticos y productos naturales.
La síntesis eficiente de piperidinas estructuralmente diversas sigue siendo un desafío clave en la química orgánica.

Objetivo del estudio:

Desarrollar una nueva reacción de tres componentes para la síntesis de complejos derivados de piperidina.
Para utilizar los iones N-alkenil iminio como intermediarios clave en las reacciones de cicloadición.

Principales métodos:

Empleando iones de N-alkenil iminio como 2-azadienos catiónicos en reacciones de [4 + 2] cicloadición.
Utilizando dienófilos de alqueno ricos en electrones y neutros.
Realización de adición nucleofílica in situ al conducto de carga cíclica.

Principales resultados:

Cícloadiciones [4 + 2] endo o exo selectivas logradas. adiciones.
Los iones de tetrahidropiridinium generados como conductos de carga cíclica iniciales.
Se han sintetizado con éxito derivados de piperidina estructuralmente y estereoquímicamente diversos.

Conclusiones:

La reacción de tres componentes desarrollada proporciona una síntesis versátil y eficiente de piperidinas complejas.
Este método amplía la caja de herramientas sintéticas para acceder a andamios de piperidina médicamente relevantes.

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