Issue 13, 2015

Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

Abstract

Nitrogen heterocycles are abundant in natural products and pharmaceuticals. An emerging interest among synthetic chemists is to apply vinyl azides as a pivotal three-atom synthon for the construction of structurally complex and diverse N-heterocyclic skeletons. The unique features of the azide group connected to an alkene moiety permit vinyl azides to function as electrophiles, nucleophiles, or radical acceptors; their access to diverse reaction pathways provides great opportunities to generate highly reactive intermediates with often unusual or unconventional reactivities. This tutorial review will systematically illustrate the reactivities of vinyl azides and describe recent breakthroughs in the development of new transformations that create N-heterocycles.

Graphical abstract: Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

Article information

Article type
Review Article
Submitted
17 Jan 2015
Accepted
18 Feb 2015
First published
18 Feb 2015

Org. Biomol. Chem., 2015,13, 3844-3855

Author version available

Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

B. Hu and S. G. DiMagno, Org. Biomol. Chem., 2015, 13, 3844 DOI: 10.1039/C5OB00099H

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