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Catalytic Cyclization of o‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines |
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| Authors: | Andrea Álvarez‐Pérez Dr Carlos González‐Rodríguez Dr Cristina García‐Yebra Dr Jesús A Varela Dr Enrique Oñate Prof Miguel A Esteruelas Prof Carlos Saá |
| Institution: | 1. Departamento de Química Orgánica and Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela (Spain);2. Departamento de Química Inorgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Centro de Innovación de Química Avanzada (ORFEO‐CINQA), Universidad de Zaragoza‐CSIC, 50009 Zaragoza (Spain) |
| Abstract: | 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. |
| Keywords: | benzazepines cyclization metallacyclopropenes osmium catalysts phenethylamines |