Application of organic azides for the synthesis of nitrogen-containing molecules

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-Azido-cyclobutanols 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. © Georg Thieme Verlag Stuttgart. New York.