New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold

In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular SNAr and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehy...

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Detalles Bibliográficos
Autores: Moreno, David, Giorgi, Giorgio, Salas, Cristian, Tapia, Ricardo
Tipo de recurso: artículo
Fecha de publicación:2013
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/34392
Acceso en línea:https://hdl.handle.net/20.500.14352/34392
Access Level:acceso abierto
Palabra clave:547
dibenzoxepins
Wittig reaction
McMurry reaction
aromatic nucleophilic substitution
Química orgánica (Farmacia)
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spelling New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin ScaffoldMoreno, DavidGiorgi, GiorgioSalas, CristianTapia, Ricardo547dibenzoxepinsWittig reactionMcMurry reactionaromatic nucleophilic substitutionQuímica orgánica (Farmacia)In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular SNAr and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehydes with fluorobenzaldehydes without catalysts. Application of an intramolecular McMurry reaction to the synthesized diarylethers using TiCl4/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%–55% yields.MDPIUniversidad Complutense de Madrid20132013-11-2620132013-11-26journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/34392reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Atribución 3.0 Españahttps://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/343922026-06-02T12:44:21Z
dc.title.none.fl_str_mv New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
spellingShingle New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
Moreno, David
547
dibenzoxepins
Wittig reaction
McMurry reaction
aromatic nucleophilic substitution
Química orgánica (Farmacia)
title_short New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_full New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_fullStr New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_full_unstemmed New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_sort New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
dc.creator.none.fl_str_mv Moreno, David
Giorgi, Giorgio
Salas, Cristian
Tapia, Ricardo
author Moreno, David
author_facet Moreno, David
Giorgi, Giorgio
Salas, Cristian
Tapia, Ricardo
author_role author
author2 Giorgi, Giorgio
Salas, Cristian
Tapia, Ricardo
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
dibenzoxepins
Wittig reaction
McMurry reaction
aromatic nucleophilic substitution
Química orgánica (Farmacia)
topic 547
dibenzoxepins
Wittig reaction
McMurry reaction
aromatic nucleophilic substitution
Química orgánica (Farmacia)
description In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular SNAr and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehydes with fluorobenzaldehydes without catalysts. Application of an intramolecular McMurry reaction to the synthesized diarylethers using TiCl4/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%–55% yields.
publishDate 2013
dc.date.none.fl_str_mv 2013
2013-11-26
2013
2013-11-26
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/34392
url https://hdl.handle.net/20.500.14352/34392
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución 3.0 España
https://creativecommons.org/licenses/by/3.0/es/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución 3.0 España
https://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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