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Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A Combined Experimental and Theoretical Study

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Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A Combined Experimental and Theoretical Study

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dc.contributor.author Monleon, 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 2014-11-12T08:34:22Z
dc.date.issued 2013-10-25
dc.identifier.issn 0947-6539
dc.identifier.uri http://hdl.handle.net/10251/44095
dc.description.abstract A very efficient synthesis of 5-halogen-1,3-oxazin-2-ones has been accomplished by the halocyclisation reaction of chiral nonracemic N-carbobenzyloxy (N-Cbz)-protected propargylic amines by using I-2, Br-2 and Cl-2 as electrophile sources. The nature of the halogen influences the reaction time and yield. However, in all cases the reaction is totally regioselective taking place through a 6-endo-dig process regardless of the nature of the halogen and of the substituents in the starting material. To rationalise the experimental results, theoretical studies at the B3LYP/6-311G* level have been performed. es_ES
dc.description.sponsorship Financial support from the MINECO (Gobierno de Espana) and FEDER (European Union) (CTQ2009-13083) and from Generalitat Valenciana (ACOMP2012-212 and ISIC2012/001) is gratefully acknowledged. A.M. thanks the Generalitat Valenciana for a predoctoral grant. en_EN
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation MINECO (Gobierno de Espana) es_ES
dc.relation FEDER (European Union) CTQ2009-13083 es_ES
dc.relation Generalitat Valenciana ACOMP2012-212 ISIC2012/001 es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Density functional calculations es_ES
dc.subject Halocyclisation es_ES
dc.subject Oxazinones es_ES
dc.subject Propargylic amines es_ES
dc.subject Reaction mechanisms es_ES
dc.subject Regioselectivity es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A Combined 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/chem.201302089
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 Monleon, A.; Blay, G.; Domingo, LR.; Muñoz Roca, MDC.; Pedro, JR. (2013). Synthesis of Densely Functionalised 5-Halogen-1,3-oxazin-2-ones byHalogen-Mediated Regioselective Cyclisation of N-Cbz-ProtectedPropargylic Amines: A Combined Experimental and Theoretical Study. Chemistry - A European Journal. 19(44):14852-14860. doi:10.1002/chem.201302089 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/chem.201302089 es_ES
dc.description.upvformatpinicio 14852 es_ES
dc.description.upvformatpfin 14860 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 19 es_ES
dc.description.issue 44 es_ES
dc.relation.senia 260786


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