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Síntesis altamente eficiente de N-heterociclos catalizada por Cu (I) a través de una adición de alquinas

Junbin Han¹, Bo Xu, Gerald B Hammond

¹Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.

Journal of the American Chemical Society

|January 1, 2010

Resumen

La catálisis del cobre permite una síntesis de un solo recipiente de N-heterociclos funcionalizados a partir de aminoalquinas y alquinas terminales. Este proceso de hidroaminación/alquinilación en tándem produce de manera eficiente anillos de cinco, seis y siete miembros.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química Heterocíclica La Química Heterocíclica es una de las más conocidas.

Sus antecedentes:

Los N-heterociclos son frecuentes en productos farmacéuticos y productos naturales.
La síntesis eficiente de diversos andamios N-heterocíclicos es crucial para el descubrimiento de medicamentos.
Las reacciones en tándem ofrecen un acceso simplificado a arquitecturas moleculares complejas.

Objetivo del estudio:

Desarrollar un novedoso método de una sola olla para sintetizar N-heterociclos funcionalizados.
Para utilizar el cobre ((I) la catálisis para una secuencia en tándem de hidroaminación/alquinilación.
Para explorar el alcance de los aminoalquinos y sustratos alquinos terminales.

Principales métodos:

Reacción catalizada por cobre de las aminoalquinas (terminales o internas) con las alquinas terminales.
Proceso de una sola olla, en tándem de hidroaminación y alquinilación.
Caracterización de los N-heterociclos resultantes de cinco, seis y siete miembros.

Principales resultados:

Se lograron excelentes rendimientos de N-heterociclos funcionalizados.
La reacción acomoda tanto las aminoalquinas terminales como las internas.
Diversos productos heterocíclicos N de cinco, seis y siete miembros fueron sintetizados con éxito.

Conclusiones:

La reacción en tándem catalizada por Cu (I) desarrollada proporciona una ruta eficiente a los valiosos heterociclos N.
Este método ofrece un enfoque práctico para la construcción de complejos marcos heterocíclicos.
La metodología tiene potencial para aplicaciones en química medicinal y ciencia de materiales.

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