α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles
| Autor: | Abderrahman El Bouakher, Sébastien Comesse, Arnaud Martel |
|---|---|
| Přispěvatelé: | Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), Normandie Université (NU)-Normandie Université (NU), Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2019 |
| Předmět: |
Reaction conditions
[CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Organic Chemistry Substituent 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Domino Cycloaddition 0104 chemical sciences chemistry.chemical_compound Nitrogen atom chemistry Amide [CHIM]Chemical Sciences Reactivity (chemistry) Physical and Theoretical Chemistry |
| Zdroj: | Organic and Biomolecular Chemistry Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (37), pp.8467-8485. ⟨10.1039/C9OB01683J⟩ |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c9ob01683j |
| Popis: | International audience; This review provides an overview of the applications of α-halogenoacetamides in domino and cycloaddition reactions. α-Halogenoacetamides are versatile building blocks that can lead to a wide variety of complex aza-heterocycles of biological interest when engaged in domino and/or cycloaddition reactions. The reactivity and the reaction conditions involved for these species (solvent, base, etc.) are closely related to the substituent onto the nitrogen atom of the amide: N-alkyl α-halogenoacetamides usually act as formal 1,3-dipoles in domino processes whereas N-alkoxy derivatives often react as real 1,3-dipoles via the formation of aza-oxyallyl cation species. This important modulation of the reactivity of these compounds opens the way to a large panel of reactions and therefore to a large diversity of aza-heterocycles. |
| Databáze: | OpenAIRE |
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