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5-Alkenylthiazoles as In-Out Dienes in Polar [4+2] Cycloaddition Reactions

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dc.contributor.authorAlajarín, Mateo
dc.contributor.authorCabrera, Jose
dc.contributor.authorSanchez-Andrada, Pilar
dc.contributor.authorBautista, Delia
dc.contributor.authorPastor Vivero, Aurelia
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-11-03T17:15:46Z
dc.date.available2021-11-03T17:15:46Z
dc.date.issued2013-09-25
dc.description.abstract5-Alkenyl-2-aminothiazoles react as in-out dienes with a wide range of electron-poor dienophiles leading to the corresponding cycloaddition products in good to excellent yields. The [4+2] cycloadditions of 5-alkenyl-2-aminothiazoles can be classified as site-selective since only the diene moiety including the formal C-C double bond of the heterocycle and that of the side-chain is involved. Calculations of the HOMO energy values of representative 5-alkenyl-2-aminothiazoles are disclosed The cycloadditions are endo-selective with N-phenylmaleimide or maleic anhydride and regioselective when the reactions are conducted with non symmetrical dienophiles. Completely oxidized cycloadducts are obtained in the reactions of 5-alkenyl-2-aminothiazoles with naphthoquinone or DMAD. Unexpectedly, the reactions with PTAD are not stereospecific. A mechanism placed at the concerted/stepwise boundary is proposed.es
dc.formatapplication/pdfes
dc.format.extent12es
dc.identifier.citationEuropean Journal Organic Chemistry, 2013, 7500–7511
dc.identifier.doi10.1002/ejoc.201300925
dc.identifier.issn1434-193X (print) 1099-0690 (web)
dc.identifier.urihttp://hdl.handle.net/10201/113645
dc.languageenges
dc.publisherWileyes
dc.relationNombre del proyecto: Reagrupamientos [1,n]-H en heterocumulenos y preparación de nuevos [2]-rotaxanos y lanzaderas moleculares. Código: 08661/PI/08. Agencia/entidad financiadora: Fundación Séneca-CARM, Consejería de Educación, Ciencia e Investigación. Ámbito Regional. Ayudas para la realización de proyectos de investigación. Programa Séneca 2008. Convocatoria 2008.es
dc.relation.publisherversionhttps://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201300925es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectSynthetic methodses
dc.subjectCycloadditiones
dc.subjectCyclizationes
dc.subjectZwitterionses
dc.subjectReaction mechanismes
dc.subjectNitrogen heterocycleses
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.title5-Alkenylthiazoles as In-Out Dienes in Polar [4+2] Cycloaddition Reactionses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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