1,3,5-Oxadiazine Framework by Oxygen vs. Nitrogen Trapping of an N-Acyliminium Ion Derived from N,O-bis-TMS Pyroglutamic Acid
| Autor: | Cristina-Maria Abuhaie, Alina Ghinet, Joëlle Dubois, Benoît Rigo, Hamid Marzag, Emmanuelle Lipka, Germain Homerin, Adam Daïch |
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| Přispěvatelé: | Lille Inflammation Research International Center - U 995 (LIRIC), Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille), Alexandru Ioan Cuza University of Iași [Romania], Hautes Etudes d’Ingénieur [Lille] (HEI), Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), Normandie Université (NU)-Normandie Université (NU), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Lille 2 - Faculté de Médecine, The authors gratefully acknowledge the 'Fondation de La Catho de Lille', the French School of High Studies in Engineering (HEI), the 'Métropole Européenne de Lille' (MEL) for the PhD scholarship attributed to one of us G.H and the University of Le Havre Normandie for technical and financial aids., JUNIA (JUNIA), Université catholique de Lille (UCL)-Université catholique de Lille (UCL), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculté de Médecine Henri Warembourg - Université de Lille |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
5-Oxadiazine
010405 organic chemistry Bis-N Inorganic chemistry N-Acyliminium chemistry.chemical_element General Chemistry Trapping 010402 general chemistry 01 natural sciences Oxygen Nitrogen Pyroglutamic acid 0104 chemical sciences Ion chemistry.chemical_compound chemistry O-Acetal Organic chemistry [CHIM]Chemical Sciences Heterocyclisation |
| Zdroj: | ChemistrySelect ChemistrySelect, Wiley, 2017, 2 (33), pp.10654-10660. ⟨10.1002/slct.201701766⟩ ChemistrySelect, 2017, 2 (33), pp.10654-10660. ⟨10.1002/slct.201701766⟩ |
| ISSN: | 2365-6549 |
| DOI: | 10.1002/slct.201701766⟩ |
| Popis: | International audience; We report that the reaction of N,O-bis-TMS pyroglutamic acid with aldehydes, under basic or acid catalysis leads to O-bis-TMS adducts. Treatment of these N,O-acetals by TfOH affords azalactones or N,N′-substituted methylene-bis-pyroglutamic acids from the trapping of N-acyliminium species, respectively, with oxygen or nitrogen atom intramolecularly versus intermolecularly. Anodic oxidation of the amido acids, followed by diastereoselective oxa-cyclisation of new N-acyliminium salts, provides exclusively fused meso-1,3,5-oxadiazines with the stereochemistry secured by X-ray analysis. The reactivity of these skeletons under both alkaline and acid conditions was also envisioned and discussed. © 2017 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim |
| Databáze: | OpenAIRE |
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