Jump to main content
Jump to site search

Issue 37, 2019
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Publication details

The article was received on 30 Jul 2019, accepted on 30 Aug 2019 and first published on 30 Aug 2019


Article type: Review Article
DOI: 10.1039/C9OB01683J
Org. Biomol. Chem., 2019,17, 8467-8485

  •   Request permissions

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

    A. El Bouakher, A. Martel and S. Comesse, Org. Biomol. Chem., 2019, 17, 8467
    DOI: 10.1039/C9OB01683J

Search articles by author

Spotlight

Advertisements