Application of Organic Azides
for the Synthesis of Nitrogen-Containing Molecules

Shunsuke Chiba

doi:10.1055/s-0031-1290108

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Synlett 2012(1): 21-44
DOI: 10.1055/s-0031-1290108

ACCOUNT

Application of Organic Azides for the Synthesis of Nitrogen-Containing Molecules

Shunsuke Chiba*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: shunsuke@ntu.edu.sg;

Further Information

Publication History

Received 31 May 2011
Publication Date:
09 December 2011 (online)

Abstract
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Abstract

In this account, recent advances made on the reactions of several types of organic azides, such as vinyl azides, cyclic 2-azido alcohols, α-azido carbonyl compounds, towards the synthesis of nitrogen-containing molecules are described.

1 Introduction

2 Chemistry of Vinyl Azides

2.1 Thermal [3+2]-Annulation of Vinyl Azides with 1,3-Dicarbonyl Compounds

2.2 Manganese(III)-Catalyzed Formal [3+2]-Annulation with 1,3-Dicarbonyl Compounds

2.3 Manganese(III)-Mediated/Catalyzed Formal [3+3]-Annulation with Cyclopropanols

2.4 Synthesis of Isoquinolines from α-Aryl-Substituted Vinyl Azides and Internal Alkynes by Rhodium-Copper Bimetallic Cooperation

3 Chemistry of Cyclic 2-Azido Alcohols

3.1 Manganese(III)-Catalyzed Ring Expansion of 2-Azidocyclobutanols

3.2 Palladium(II)-Catalyzed Ring Expansion of Cyclic 2-Azido Alcohols

4 Chemistry of α-Azido Carbonyl Compounds

4.1 Orthogonal Synthesis of Isoindole and Isoquinoline Derivatives

4.2 Generation of Iminylcopper Species and Their Catalytic Carbon-Carbon Bond Cleavage under an Oxygen Atmosphere

4.3 Copper(II)-Catalyzed Aerobic Synthesis of Azaspirocyclohexadienones

5 Conclusion

Key words

azides - nitrogen-containing heterocycles - radical reactions - redox reactions - oxygenations

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Wang, Y.-F.; Toh, K. K.; Chiba, S. unpublished results.