Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: Microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives
| Autor: | Yoann Rousselin, Christopher Golz, Houda Gazzeh, Moheddine Askri, Abderrahim Khatyr, Carsten Strohmann, Michael Knorr, Sarra Boudriga, Marek M. Kubicki |
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| Přispěvatelé: | Faculté des Sciences de Monastir (FSM), Université de Monastir - University of Monastir (UM), Univers, Transport, Interfaces, Nanostructures, Atmosphère et environnement, Molécules (UMR 6213) (UTINAM), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Franche-Comté (UFC), Université Bourgogne Franche-Comté [COMUE] (UBFC)-Université Bourgogne Franche-Comté [COMUE] (UBFC), Technische Universität Dortmund [Dortmund] (TU), Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB), Centre National de la Recherche Scientifique (CNRS)-Université de Bourgogne (UB)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry General Chemical Engineering General Chemistry 010402 general chemistry 01 natural sciences Fluorescence Microwave assisted Cycloaddition 0104 chemical sciences Adduct Computational chemistry Dehydrohalogenation Organic chemistry [CHIM]Chemical Sciences Luminescence Stoichiometry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | RSC Advances RSC Advances, Royal Society of Chemistry, 2016, 6, pp.49868-49875. ⟨10.1039/C6RA09703K⟩ |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/C6RA09703K⟩ |
| Popis: | Microwave-assisted 1,3-dipolar cycloaddition of (E,E)-1,3-bisarylidenetetral-2-ones with nitrilimines, generated in situ by dehydrohalogenation of the corresponding hydrazonoyl chlorides, affords a series of spiropyrazolines in good to excellent yields. The presence of a second exocyclic CC bond also allows the preparation of dispiropyrazolines. The cycloaddition proceeds with high chemo-, regio- and diastereoselectivity. The structure of the spiranic adducts has been established on the basis of their spectroscopic data and elemental analyses. The stereochemistry of these N-heterocycles has been confirmed by two X-ray diffraction studies. The luminescence properties and fluorescence quantum yields of these heterocyclic compounds have been investigated revealing that some of them are fluorescent in solution. |
| Databáze: | OpenAIRE |
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