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Transferencia de nitreno catalizado por plata quimioselectiva: Síntesis sintéticas de las azepinas y los
Emily Z Schroeder1, Chenxi Lin1, Yun Hu1
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue ,Madison, Wisconsin 53706, United States.
Journal of the American Chemical Society
|July 25, 2024
Resumen
Este estudio introduce un nuevo método catalizado por plata para sintetizar azepinas, compuestos cruciales para el descubrimiento de fármacos. El proceso eficiente permite transformaciones químicas selectivas, ampliando la disponibilidad de estos importantes andamios moleculares.
Área de la Ciencia:
- Química orgánica
- Química medicinal
- Catálisis
Sus antecedentes:
- Las azepinas y las azepanas son motivos estructurales vitales en compuestos biológicamente activos.
- Estos importantes andamios están actualmente subrepresentados en las bibliotecas de detección de drogas.
Objetivo del estudio:
- Desarrollar un método suave y eficiente para la síntesis de la azepina.
- Para permitir la diversificación de las azepinas en etapa tardía para la construcción de moléculas complejas.
Principales métodos:
- Reacción de transferencia de nitreno dearomativo catalizado por plata.
- Se utilizó un precursor de nitreno de carbamimidato protegido por 2,2,2-tricloroetoxisulfonilo (Tces).
- Se empleó un ligando de plata específico para controlar la quimioselectividad.
Principales resultados:
- Se logró una quimioselectividad inesperada entre la desaromatización de areno y la aminación bencílica C ((sp3) -H.
- Demostró una vía leve y eficiente para la formación de azepina.
- Potencial destacado para la diversificación en etapa tardía y la hidrogenación diastereoselectiva.
Conclusiones:
- El método desarrollado proporciona una nueva vía valiosa para los andamios de azepina.
- Este enfoque aumenta la utilidad de las azepinas en la química medicinal y el descubrimiento de fármacos.
- El control quimioselectivo ofrece oportunidades para crear diversas arquitecturas moleculares.
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