The Cyanamide Moiety, Synthesis and Reactivity

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

Key words

cyanamide - cyanation - nitrogen - heterocycles - nitrogen ligands

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