Catalytic Cyclization of o ‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines
| Autor: | Cristina García-Yebra, Carlos Gonzalez‐Rodriguez, Carlos Saá, Enrique Oñate, Jesús A. Varela, Andrea Álvarez-Pérez, Miguel A. Esteruelas |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (España), Diputación General de Aragón, European Commission, Ministerio de Ciencia e Innovación (España), Xunta de Galicia, Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares, Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Rok vydání: | 2015 |
| Předmět: |
Models
Molecular Phenethylamine Benzazepines Stereochemistry Dopamine Phenethylamines Crystallography X-Ray Catalysis Benzazepine chemistry.chemical_compound Organometallic Compounds Molecule Osmium catalysts Molecular Structure Dopaminergic General Medicine General Chemistry Osmium Metallacyclopropenes chemistry Cyclization Alkynes |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela Minerva: Repositorio Institucional de la Universidad de Santiago de Compostela Universidad de Santiago de Compostela (USC) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201505782 |
| Popis: | 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. This research was supported by the MICINN (projects CTQ2011-28258, CTQ2014-52799-P, and CTQ2014-51912REDC), Xunta de Galicia and the European Regional Development Fund (projects GRC2014/032 and EM 2012/051), the DGA (E-35), and the European Social Fund (SFE). A.A.-P.and C.G.-R. thank the Spanish MICINN for a pre-doctoral FPI fellowship and Juan de la Cierva Contract (JCI-2011-09946), respectively. |
| Databáze: | OpenAIRE |
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