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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
La transanulación catalizada por el rodio de 1,2,3-triazoles con nitriles
Tony Horneff1, Stepan Chuprakov, Natalia Chernyak
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|October 16, 2008
Resumen
Los triazoles 1-sulfonilo estables se convierten fácilmente en imidazoles mediante reacciones catalizadas por el rodio (II) con nitriles. Esta síntesis eficiente ofrece una nueva ruta a valiosos compuestos de imidazol.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- La catálisis es la catálisis.
Sus antecedentes:
- Los triazoles 1-sulfonilo son precursores estables y accesibles.
- Los imidazoles son importantes compuestos heterocíclicos con diversas aplicaciones.
- Se buscan continuamente métodos sintéticos eficientes para los imidazoles.
Objetivo del estudio:
- Desarrollar un nuevo método para sintetizar imidazoles.
- Para utilizar los triazoles 1-sulfonilo fácilmente disponibles como materiales de partida.
- Para explorar las transformaciones catalizadas por el rodio (II).
Principales métodos:
- Reacción de los triazoles 1-sulfonilo con los nitriles.
- Empleando el rodio (II) catalizadores.
- Caracterización de los productos de reacción.
Principales resultados:
- Se logró la conversión de triazoles 1-sulfonilo en imidazoles.
- Se han reportado rendimientos de buenos a excelentes para los productos de imidazol.
- Se propone el uso de los iminocarbenoides de rodio como intermediarios clave de la reacción.
Conclusiones:
- Se establece un nuevo método catalizado por rodio para la síntesis de imidazol a partir de triazoles 1-sulfonilo.
- La reacción procede de manera eficiente, proporcionando altos rendimientos de imidazoles.
- El mecanismo propuesto involucra intermediarios de iminocarbenoide de rodio.
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