Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivatives
| Autor: | Jean-François Lohier, Vincent Reboul, Flavie Peudru, Mihaela Gulea |
|---|---|
| Přispěvatelé: | Laboratoire de chimie moléculaire et thioorganique (LCMT), Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU), Laboratoire d'Innovation Thérapeutique (LIT), Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2016 |
| Předmět: |
010402 general chemistry
01 natural sciences Biochemistry Aldehyde Inorganic Chemistry chemistry.chemical_compound 4-thiazepine Thiazine Organic chemistry Thiazepine Three-component reaction β-lactam-condensed 1 Staudinger reaction Thioamide chemistry.chemical_classification 3-thiazine [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Alkene Organic Chemistry Diastereomer 3. Good health 0104 chemical sciences chemistry Lactam |
| Zdroj: | Phosphorus, Sulfur, and Silicon and the Related Elements Phosphorus, Sulfur, and Silicon and the Related Elements, Taylor & Francis, 2016, 191 (2), pp.220-229. ⟨10.1080/10426507.2015.1072191⟩ |
| ISSN: | 1563-5325 1042-6507 |
| DOI: | 10.1080/10426507.2015.1072191 |
| Popis: | International audience; Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by stereoselective Staudinger reaction into the corresponding chloro-β-lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one β-lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry. |
| Databáze: | OpenAIRE |
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