Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines
| Autor: | Olivier Chavignon, Alain Gueiffier, Gregory Delmas, Emmanuel Moreau, Y. Blache, Claire Lartigue, Gérard Grassy, Jean C. Teulade, Jean M. Chezal |
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| Přispěvatelé: | Imagerie Moléculaire et Stratégies Théranostiques (IMoST), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020]), Nutrition, croissance et cancer (U 1069) (N2C), Université de Tours (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM), Laboratoire Matériaux Polymères Interfaces Environnement Marin - EA 4323 (MAPIEM), Université de Toulon (UTLN), Laboratoire Universitaire de Recherche en Production Automatisée (LURPA), École normale supérieure - Cachan (ENS Cachan)-Université Paris-Sud - Paris 11 (UP11), Université de Tours-Institut National de la Santé et de la Recherche Médicale (INSERM), Université Paris-Sud - Paris 11 (UP11)-École normale supérieure - Cachan (ENS Cachan), Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Institut National de la Santé et de la Recherche Médicale (INSERM) |
| Rok vydání: | 2001 |
| Předmět: |
Annulation
[CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Chemistry Organic Chemistry Ab initio [CHIM.THER]Chemical Sciences/Medicinal Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound [CHIM.COOR]Chemical Sciences/Coordination chemistry Thermal reaction [CHIM.RADIO]Chemical Sciences/Radiochemistry ComputingMilieux_MISCELLANEOUS Carbodiimide |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, 2001, 66 (20), pp.6576-6584. ⟨10.1021/jo015582x⟩ Journal of Organic Chemistry, American Chemical Society, 2001, 66 (20), pp.6576-6584. ⟨10.1021/jo015582x⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-a]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-, (x = 5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed. |
| Databáze: | OpenAIRE |
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