title: Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines.
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.
authors.affiliation: 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).
authors.forename: Andrea
authors.initials: A
authors.lastname: Álvarez-Pérez
authors.affiliation: 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).
authors.forename: Carlos
authors.initials: C
authors.lastname: González-Rodríguez
authors.affiliation: 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).
authors.forename: Cristina
authors.initials: C
authors.lastname: García-Yebra
authors.affiliation: 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).
authors.forename: Jesús A
authors.initials: JA
authors.lastname: Varela
authors.affiliation: 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).
authors.forename: Enrique
authors.initials: E
authors.lastname: Oñate
authors.affiliation: 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). maester@unizar.es.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Esteruelas
authors.affiliation: 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). carlos.saa@usc.es.
authors.forename: Carlos
authors.initials: C
authors.lastname: Saá
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004298:Dopamine / Q000378:metabolism*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D009992:Osmium / Q000737:chemistry*; D010627:Phenethylamines / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001552:Benzazepines; D009942:Organometallic Compounds; D010627:Phenethylamines; D009992:Osmium; C029261:phenethylamine; D004298:Dopamine
keywords: benzazepines; cyclization; metallacyclopropenes; osmium catalysts; phenethylamines