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10.1002/ejoc.201300925
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Título: | 5-Alkenylthiazoles as In-Out Dienes in Polar [4+2] Cycloaddition Reactions |
Fecha de publicación: | 25-sep-2013 |
Editorial: | Wiley |
Cita bibliográfica: | European Journal Organic Chemistry, 2013, 7500–7511 |
ISSN: | 1434-193X (print) 1099-0690 (web) |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | Synthetic methods Cycloaddition Cyclization Zwitterions Reaction mechanism Nitrogen heterocycles |
Resumen: | 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. |
Autor/es principal/es: | Alajarín, Mateo Cabrera, Jose Sanchez-Andrada, Pilar Bautista, Delia Pastor Vivero, Aurelia |
Facultad/Departamentos/Servicios: | Química Orgánica |
Versión del editor: | https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201300925 |
URI: | http://hdl.handle.net/10201/113645 |
DOI: | 10.1002/ejoc.201300925 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 12 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Aparece en las colecciones: | Artículos: Química Orgánica |
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13EJOC7500.pdf | 960,71 kB | Adobe PDF | Visualizar/Abrir |
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