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DOI: 10.1055/s-0031-1290108
Application of Organic Azides for the Synthesis of Nitrogen-Containing Molecules
Publikationsverlauf
Publikationsdatum:
09. Dezember 2011 (online)
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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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