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Sc(OTf)(3)-Mediated [4+2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction

dc.contributor.authorJiménez de Aberásturi González, Xabier
dc.contributor.authorPalacios Gambra, Francisco Javier ORCID
dc.contributor.authorDe los Santos Ruiz, Jesús Manuel ORCID
dc.date.accessioned2022-11-02T17:34:37Z
dc.date.available2022-11-02T17:34:37Z
dc.date.issued2022
dc.identifier.citationJournal of Organic Chemistry 87(17) : 11583-11592 (2022)es_ES
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/10810/58240
dc.description.abstractWe disclose the first accomplishment of the azo-Povarov reaction involving Sc(OTf)3-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offers a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product.es_ES
dc.description.sponsorshipFinancial support by the Ministerio de Ciencia, Innovacion y Universidades (MCIU), Agencia Estatal de Investigacion (AEI) y Fondo Europeo de Desarrollo Regional (FEDER) (RTI2018-101818-B-I00, UE), and Gobierno Vasco (GV, IT 992-16) is gratefully acknowledged. X.J.-A. thanks the Basque Country Government for the granted predoctoral fellowship. The authors thank technical and human support provided by SGIker (UPV/EHU/ERDF, EU).es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.relationinfo:eu-repo/grantAgreement/MICIU/RTI2018-101818-B-I00es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.subjectDiels-Alder reactiones_ES
dc.subjecttopoisomerase-i inhibitorses_ES
dc.subjectbiological evaluationes_ES
dc.subjectfacile synthesises_ES
dc.subjectLewis-acides_ES
dc.subjectheterocycleses_ES
dc.subject1,2-diaza-1,3-butadieneses_ES
dc.subjecttetrahydroquinolineses_ES
dc.subjectcyclizationes_ES
dc.subjectantifungales_ES
dc.titleSc(OTf)(3)-Mediated [4+2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reactiones_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2022 The Authors. Published by American Chemical Society uncer a Creative Commons Licence Attribution 4.0 International (CC BY 4.0)es_ES
dc.rights.holderAtribución 3.0 España*
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.2c01224es_ES
dc.identifier.doi10.1021/acs.joc.2c01224
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES


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© 2022 The Authors. Published by American Chemical Society uncer a Creative Commons Licence Attribution 4.0 International (CC BY 4.0)
Except where otherwise noted, this item's license is described as © 2022 The Authors. Published by American Chemical Society uncer a Creative Commons Licence Attribution 4.0 International (CC BY 4.0)