The Cyanamide Moiety, Synthesis and Reactivity

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 <i>N</i>-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 <i>tert</i>-Butyl-<i>N</i>-chloro­cyanamide 4.5 Cyanamides as Radical Partners 5 Coordination Chemistry of Cyanamides 6 Conclusion