Catalytic Cyclization of o‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines

Thumbnail Image

Files

Angew. Chem. Int. Ed. 2015, 54, 13357-13361.pdf (281.45 KB)
Identifiers
URI: http://hdl.handle.net/10347/23347
ISSN: 1433-7851
E-ISSN: 1521-3773
DOI: 10.1002/anie.201505782

Publication date

2015

Authors

Advisors

Tutors

Editors

Journal Title

Journal ISSN

Volume Title

Publisher

Wiley
Metrics
Google Scholar
lacobus
Export

Research Projects

Organizational Units

Journal Issue

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.

Description

NOTICE: This is the peer reviewed version of the following article: Álvarez-Pérez, A., González-Rodríguez, C., García-Yebra, C., Varela, J. A., Oñate, E., Esteruelas, M. A., Saá, C. (2015). Catalytic Cyclization of o‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines. Angew. Chem. Int. Ed., 54, 45, 13357-13361. [doi: 10.1002/anie.201505782]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving

Keywords

Benzazepines| Cyclization| Metallacyclopropenes| Osmium catalysts| Phenethylamines

Bibliographic citation

Álvarez-Pérez, A., González-Rodríguez, C., García-Yebra, C., Varela, J. A., Oñate, E., Esteruelas, M. A., Saá, C. (2015). Catalytic Cyclization of o‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines. Angew. Chem. Int. Ed., 54, 45, 13357-13361

Relation

Has part

Has version

Is based on

Is part of

Is referenced by

Is version of

Requires

Sponsors

This work was supported by MICINN (projects CTQ2011-28258, CTQ2014-52799-P, and CTQ2014-51912REDC), Xunta de Galicia and 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 Spanish MICINN for a predoctoral FPI fellowship and Juan de la Cierva Contract (JCI-2011-09946), respectively

Rights

© 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving

Collections

Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica