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Redox-neutral α-oxigenación de aminas: desarrollo de la reacción y aclaración del mecanismo

Matthew T Richers¹, Martin Breugst, Alena Yu Platonova

¹Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.

Journal of the American Chemical Society

|April 3, 2014

Resumen

Este estudio introduce un nuevo método libre de catalizadores para sintetizar estructuras de benzo[e][1,3]oxazina a partir de aminas secundarias cíclicas e hidroxibenzaldehidratos. El proceso eficiente evita los oxidantes externos y revela el papel catalítico del ácido acético.

Área de la Ciencia:

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

Sus antecedentes:

La síntesis tradicional de las estructuras de benzo[e][1,3]oxazina a menudo requiere condiciones adversas, catalizadores metálicos o oxidantes externos.
El desarrollo de metodologías sintéticas eficientes y sostenibles es crucial en la química orgánica.

Objetivo del estudio:

Desarrollar un nuevo método redox-neutral para la síntesis de estructuras de benzo[e][1,3]oxazina.
Investigar el papel catalítico del ácido acético en esta transformación.
Explorar vías de reacción alternativas, incluida la aminación reductiva.

Principales métodos:

Reacción de aminas secundarias cíclicas con 2-hidroxibenzaldehídos o cetonas relacionadas.
Catálisis ácida con el uso de ácido acético.
Cálculos de la teoría funcional de la densidad (DFT) para la investigación mecanicista.

Principales resultados:

En general, se lograron buenos rendimientos de las estructuras de benzo[e][1,3]oxazina.
La reacción se produce a través de una vía combinada de reducción N-alquilación / oxidación α-funcionalización.
No se requerían oxidantes externos ni catalizadores metálicos.
Las condiciones modificadas produjeron o-hidroxibenzilaminas a través de una vía de aminación reductiva que involucra la oxidación de aminas.

Conclusiones:

Se ha establecido un método novedoso, eficiente y sostenible para la síntesis de benzo[e][1,3]oxazina.
El ácido acético actúa como un catalizador eficaz, y su eficiencia catalítica ha sido aclarada.
El estudio proporciona información sobre la funcionalización de la amina α-C-H y los mecanismos de aminación reductiva.

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