Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines

A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene...

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Detalles Bibliográficos
Autores: Álvarez-Pérez, Andrea, González-Rodríguez, Carlos, García-Yebra, Cristina, Varela, Jesús A., Oñate, Enrique, Esteruelas, Miguel A., Saá, Carlos
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2015
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/154635
Acceso en línea:http://hdl.handle.net/10261/154635
Access Level:acceso abierto
Palabra clave:Cyclization
Benzazepines
Phenethylamines
Osmium catalysts
Metallacyclopropenes
Descripción
Sumario:A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.