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Secuencia de acoplamiento de tres componentes para la síntesis regiospecífica de piridinas sustituidas

Ming Z Chen¹, Glenn C Micalizio

¹Kellogg School of Science and Technology at The Scripps Research Institute, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.

Journal of the American Chemical Society

|November 23, 2011

Resumen

Un nuevo método sintetiza piridinas sustituidas utilizando adición nucleofílica y reacciones mediadas por metaciclos. Este enfoque permite el ensamblaje controlado y convergente de diversas estructuras de piridina.

Área de la Ciencia:

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

Sus antecedentes:

Los derivados de piridina son andamios cruciales en los productos farmacéuticos y la ciencia de los materiales.
Los métodos sintéticos eficientes y regioselectivos para las piridinas sustituidas son muy buscados.

Objetivo del estudio:

Desarrollar una nueva síntesis de novo para la construcción de piridinas altamente sustituidas.
Para lograr un control regioquímico completo en la formación de anillos de piridina.

Principales métodos:

Adición nucleofílica de un anión dietiano a los compuestos carbonílicos α,β insaturados.
Acoplamiento mediado por ciclo metálico de alcoholes alílicos con trimetilsilano-iminas generadas in situ.
La ciclización mediada por plata ((I) o mercurio ((II).

Principales resultados:

Síntesis exitosa de di- a través de piridinas penta-sustituidas.
Demostración de un control regioquímico completo durante toda la síntesis.
Estrategia de ensamblaje convergente que permite la construcción eficiente de arquitecturas complejas de piridina.

Conclusiones:

El método descrito proporciona una ruta versátil y regioselectiva a las piridinas sustituidas.
Esta síntesis amplía el conjunto de herramientas para acceder a complejos derivados de piridina.
La estrategia es susceptible al ensamblaje convergente de diversos objetivos de piridina.

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