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10.1002/ejoc.201300925
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Alajarín, Mateo | - |
dc.contributor.author | Cabrera, Jose | - |
dc.contributor.author | Sanchez-Andrada, Pilar | - |
dc.contributor.author | Bautista, Delia | - |
dc.contributor.author | Pastor Vivero, Aurelia | - |
dc.contributor.other | Química Orgánica | es |
dc.date.accessioned | 2021-11-03T17:15:46Z | - |
dc.date.available | 2021-11-03T17:15:46Z | - |
dc.date.issued | 2013-09-25 | - |
dc.identifier.citation | European Journal Organic Chemistry, 2013, 7500–7511 | es |
dc.identifier.issn | 1434-193X (print) 1099-0690 (web) | - |
dc.identifier.uri | http://hdl.handle.net/10201/113645 | - |
dc.description.abstract | 5-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.format | application/pdf | es |
dc.format.extent | 12 | es |
dc.language | eng | es |
dc.publisher | Wiley | es |
dc.relation | Nombre 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.rights | info:eu-repo/semantics/openAccess | es |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Synthetic methods | es |
dc.subject | Cycloaddition | es |
dc.subject | Cyclization | es |
dc.subject | Zwitterions | es |
dc.subject | Reaction mechanism | es |
dc.subject | Nitrogen heterocycles | es |
dc.subject.other | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica | es |
dc.title | 5-Alkenylthiazoles as In-Out Dienes in Polar [4+2] Cycloaddition Reactions | es |
dc.type | info:eu-repo/semantics/article | es |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201300925 | es |
dc.identifier.doi | 10.1002/ejoc.201300925 | - |
Aparece en las colecciones: | Artículos: Química Orgánica |
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