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Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne Carbamate Cyclisation: An Experimental and Theoretical Study

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Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne Carbamate Cyclisation: An Experimental and Theoretical Study

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dc.contributor.author Monleón, Alicia es_ES
dc.contributor.author Blay, Gonzalo es_ES
dc.contributor.author Domingo, Luis R. es_ES
dc.contributor.author Muñoz Roca, María del Carmen es_ES
dc.contributor.author Pedro, José R. es_ES
dc.date.accessioned 2016-07-12T10:42:44Z
dc.date.issued 2015-02
dc.identifier.issn 1434-193X
dc.identifier.uri http://hdl.handle.net/10251/67460
dc.description.abstract A very efficient synthesis of 5-chalcogenyl-1,3-oxazin-2-ones has been accomplished by the chalcogen-mediated yne-carbamate cyclisation of chiral, non-racemic N-Cbz-protected propargylic amines using PhXY (X = Se, S, Te; Y = Br or Cl) as electrophile sources. The reactions gave good-toexcellent yields for a wide range of substrates. In all cases the reaction was totally regioselective, occurring by a 6-endo-dig process regardless of the nature of the reagent and of the substituents in the starting material. This methodology permits the formation of the 1,3-oxazin-2-one moiety as well as the simultaneous installation of a chalcogen functionality onto the heterocyclic ring. The experimental results have been rationalised by theoretical studies at the B3LYP/6-311G* level of theory. es_ES
dc.description.sponsorship Financial support from the Ministerio de Economia y Competitividad (MINECO), Gobierno de Espana, from the European Union (EU) (Fondos Europeos para el Desarrollo Regional (FEDER), grant numbers CTQ2009-13083 and CTQ2013-47494-P) and from the Generalitat Valenciana (grant numbers ACOMP2012-212 and ISIC2012/001 and a pre-doctoral grant to A. M.) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation.ispartof European Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Cyclization es_ES
dc.subject Regioselectivity es_ES
dc.subject Nitrogen heterocycles es_ES
dc.subject Chalcogens es_ES
dc.subject Reaction mechanisms es_ES
dc.subject Density functional calculations es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne Carbamate Cyclisation: An Experimental and Theoretical Study es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/ejoc.201403169
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2009-13083/ES/Desarrollo de nuevos procesos enantioselectivos de formación de enlaces C-C mediante catálisis asimétrica/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2013-47494-P/ES/NUEVOS RETOS EN EL DESARROLLO DE PROCESOS ENANTIOSELECTIVOS DE FORMACION DE ENLACES C-C MEDIANTE CATALISIS DUAL COOPERATIVA./ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//ACOMP%2F2012%2F212/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//ISIC2012%2F001/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada es_ES
dc.description.bibliographicCitation Monleón, A.; Blay, G.; Domingo, LR.; Muñoz Roca, MDC.; Pedro, JR. (2015). Efficient Synthesis of 5-Chalcogenyl-1,3-oxazin-2-ones by Chalcogen-Mediated Yne Carbamate Cyclisation: An Experimental and Theoretical Study. European Journal of Organic Chemistry. (5):1020-1027. https://doi.org/10.1002/ejoc.201403169 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/ejoc.201403169 es_ES
dc.description.upvformatpinicio 1020 es_ES
dc.description.upvformatpfin 1027 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.issue 5 es_ES
dc.relation.senia 293078 es_ES
dc.identifier.eissn 1099-0690
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Generalitat Valenciana es_ES
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