Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


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

Article information


Submitted
30 Jul 2019
Accepted
30 Aug 2019
First published
30 Aug 2019

Org. Biomol. Chem., 2019,17, 8467-8485
Article type
Review Article

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

Social activity

Search articles by author

Spotlight

Advertisements