Issue 37, 2019

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.

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

Article information

Article type
Review Article
Submitted
30 Jul 2019
Accepted
30 Aug 2019
First published
30 Aug 2019

Org. Biomol. Chem., 2019,17, 8467-8485

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements