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Os-catalyzed cyclization of o-(alkynyl)phenethylamines by osmacyclopropenation: an easy entry to dopaminergic 3-benzazepines

AuthorsÁlvarez-Pérez, Andrea; González-Rodríguez, Carlos; García-Yebra, Cristina CSIC ORCID; Varela, Jesús A.; Esteruelas, Miguel A. CSIC ORCID; Saá, Carlos
Issue Date2015
CitationXXXV Bienal RSEQ (2015)
AbstractHeterocyclic derivatives containing phenethylamine units have shown important dopaminergic properties. In particular, seven-membered 3-benzazepines remain as one of the most reliable structural scaffold in terms of the affinity and selectivity against the D1 receptor of mammalian brains. Metal-mediated intramolecular hydroamin(d)ations of alkynylamin(d)es have been employed as one of the typical pathways for their preparation. However, no 7-endo dig cyclization of terminal o-(alkynyl)phenthylamines to 3-benzazepines has been described. Based on our recently developed Os-catalyzed cyclization of terminal bis-homopropargylic alcohols, we now report the novel Os-catalyzed 7-endo dig cyclization of terminal o-(alkynyl)phenethylamines 1 to 3-benzazepines 2 via the formation of new osmacyclopropene intermediates I and II, which have been characterized by X-Ray analysis (L= PiPr3).
DescriptionResumen del póster presentado a la XXXV Reunión Bienal de la Real Sociedad Española de Química celebrada en A Coruña del 19 al 23 de julio de 2015.-- Tambien presentado al Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS) IUPAC International Symposium, celebrado en Sitges-Barcelona (España) del 28 de junio al 2 de julio de 2015.
Appears in Collections:(ISQCH) Comunicaciones congresos

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