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Synthesis 2012; 44(9): 1279-1292
DOI: 10.1055/s-0031-1289749
DOI: 10.1055/s-0031-1289749
review
The Cyanamide Moiety, Synthesis and Reactivity
Weitere Informationen
Publikationsverlauf
Received: 17. Januar 2012
Accepted after revision: 20. Februar 2012
Publikationsdatum:
12. April 2012 (online)
Abstract
The cyanamide moiety provides many opportunities as a building block for the synthesis of nitrogen-containing heterocycles. This review discusses the reported methods for the preparation of alkyl- and N-acylcyanamides and illustrates their reactivity vis-à-vis nucleophilic additions, cycloadditions, radical chemistry and coordination chemistry.
1 Introduction
2 Biological Relevance of the Cyanamide Moiety
3 Access to Cyanamides
3.1 Cyanation of Amines
3.2 Palladium Catalysis
3.3 Deoxygenation of Isocyanates
3.4 Desulfurization of Thioureas
4 Reactivity of Cyanamides
4.1 Nucleophilic Additions
4.2 Cycloadditions
4.3 Additions to Carbonyl Groups
4.4 Chlorinations and Oxidations with tert-Butyl-N-chlorocyanamide
4.5 Cyanamides as Radical Partners
5 Coordination Chemistry of Cyanamides
6 Conclusion
-
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