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Article dans une revue

α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

Abstract : 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.
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https://hal-univ-lemans.archives-ouvertes.fr/hal-02313870
Contributeur : Arnaud Martel <>
Soumis le : vendredi 11 octobre 2019 - 15:38:49
Dernière modification le : mercredi 25 mars 2020 - 09:21:05

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Abderrahman El Bouakher, Arnaud Martel, Sébastien Comesse. α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (37), pp.8467-8485. ⟨10.1039/C9OB01683J⟩. ⟨hal-02313870⟩

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