Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines

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...

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Detalles Bibliográficos
Autores: Álvarez-Pérez, Andrea, González-Rodríguez, Carlos, García-Yebra, Cristina, Varela, Jesús A., Oñate, Enrique, Esteruelas, Miguel A., Saá, Carlos
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2015
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/154635
Acceso en línea:http://hdl.handle.net/10261/154635
Access Level:acceso abierto
Palabra clave:Cyclization
Benzazepines
Phenethylamines
Osmium catalysts
Metallacyclopropenes
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spelling Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepinesÁlvarez-Pérez, AndreaGonzález-Rodríguez, CarlosGarcía-Yebra, CristinaVarela, Jesús A.Oñate, EnriqueEsteruelas, Miguel A.Saá, CarlosCyclizationBenzazepinesPhenethylaminesOsmium catalystsMetallacyclopropenesA 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.Peer ReviewedWiley-VCHMinisterio de Economía y Competitividad (España)Diputación General de AragónEuropean CommissionMinisterio de Ciencia e Innovación (España)Xunta de GaliciaConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2017201720152017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/154635reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912-REDCinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-Phttps://doi.org/10.1002/anie.201505782Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1546352026-05-22T06:33:51Z
dc.title.none.fl_str_mv Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
title Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
spellingShingle Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
Álvarez-Pérez, Andrea
Cyclization
Benzazepines
Phenethylamines
Osmium catalysts
Metallacyclopropenes
title_short Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
title_full Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
title_fullStr Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
title_full_unstemmed Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
title_sort Catalytic cyclization of o-alkynyl phenethylamines via osmacyclopropene intermediates: direct access to dopaminergic 3-benzazepines
dc.creator.none.fl_str_mv Álvarez-Pérez, Andrea
González-Rodríguez, Carlos
García-Yebra, Cristina
Varela, Jesús A.
Oñate, Enrique
Esteruelas, Miguel A.
Saá, Carlos
author Álvarez-Pérez, Andrea
author_facet Álvarez-Pérez, Andrea
González-Rodríguez, Carlos
García-Yebra, Cristina
Varela, Jesús A.
Oñate, Enrique
Esteruelas, Miguel A.
Saá, Carlos
author_role author
author2 González-Rodríguez, Carlos
García-Yebra, Cristina
Varela, Jesús A.
Oñate, Enrique
Esteruelas, Miguel A.
Saá, Carlos
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Diputación General de Aragón
European Commission
Ministerio de Ciencia e Innovación (España)
Xunta de Galicia
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Cyclization
Benzazepines
Phenethylamines
Osmium catalysts
Metallacyclopropenes
topic Cyclization
Benzazepines
Phenethylamines
Osmium catalysts
Metallacyclopropenes
description 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.
publishDate 2015
dc.date.none.fl_str_mv 2015
2017
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/154635
url http://hdl.handle.net/10261/154635
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912-REDC
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-P
https://doi.org/10.1002/anie.201505782
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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