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Updated: Dec 11, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Síntesis orientada a la diversidad de N, N, O- Hidroxilaminas sustituidas de alcoholes y aminas por la formación de

Jarvis Hill^1,2, Asiri A Hettikankanamalage^1,2, David Crich^1,2,3

¹Department of Pharmaceutical and Biomedical Sciences, University of Georgia, 250 West Green Street, Athens, Georgia 30602, United States.

Journal of the American Chemical Society

|August 18, 2020

Resumen

Este estudio introduce un nuevo método para sintetizar hidroxilaminas N,N,O-trisubstituidas utilizando dialquilamidas de magnesio y MTHP. Esta reacción versátil es ideal para crear diversas bibliotecas moleculares para aplicaciones químicas medicinales.

Área de la Ciencia:

Química orgánica
Química medicinal
Química sintética

Sus antecedentes:

Las hidroxilaminas N,N,O-trisubstituidas son bases valiosas en la química medicinal.
Se necesitan rutas sintéticas eficientes para acceder a diversos derivados de hidroxilamina para el descubrimiento de fármacos.

Objetivo del estudio:

Desarrollar un método nuevo y eficiente para la síntesis de hidroxilaminas N,N,O-trisubstituidas.
Explorar el alcance y la aplicabilidad de la reacción en el diseño de bibliotecas basadas en fragmentos.

Principales métodos:

Reacción de las dialquilamidas de magnesio con los peróxidos de 2-metil-2-tetrahidropiranilo (MTHP) derivados del alcohol.
Se utiliza el tetrahidrofurano como disolvente a 0 °C.
Utiliza una gama de alquil y arilaminas secundarias y MTHP primarios y secundarios derivados del alcohol.

Principales resultados:

Se obtienen buenos a excelentes rendimientos de hidroxilaminas N,N,O-trisubstituidas.
Compatibilidad demostrada con una amplia gama de aminas y MTHP.
Destacó la amplia aplicabilidad de la reacción debido a la disponibilidad de diversos materiales de partida.

Conclusiones:

El método desarrollado proporciona una vía fácil a las hidroxilaminas N,N,O-trisubstituidas.
La versatilidad de la reacción apoya su uso en el diseño de bibliotecas basadas en fragmentos para la química medicinal.
Esta síntesis ofrece una herramienta valiosa para generar nuevas entidades químicas.

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