Unlocking the Potential of Cyanamide as a Multifunctional Scaffold in Organic Synthesis

Abstract

Cyanamides are exceptionally versatile building blocks in organic synthesis, capable of being transformed into a wide range of compounds, including ureas, isoureas, thioureas, selenoureas, guanidines, hydroxyguanidines, creatinine, pyro(thio)phosphates, and various heterocyclic structures. The unique properties of cyanamide, featuring a nucleophilic amino group and an electrophilic cyano group, make it an indispensable tool in organic synthesis. Reactions involving the amino group typically follow the behavior of amines, such as alkylation and acylation reactions, though with reduced nucleophilicity. In contrast, the cyano group undergoes a broad spectrum of reactions, including addition reactions, cycloadditions, isomerizations, and complex formation. Motivated by its fascinating chemistry and broad applications, we have thoroughly investigated cyanamide to develop new reagents, such as N-tert-butyl-N-chlorocyanamide, which has proven invaluable in chlorination and oxidation reactions. Building upon these insights, we have also explored innovative synthetic routes for producing a variety of substituted hydantoins, thiohydantoins, and iminohydantoins. Additionally, the cyanamide motif has proven to be of great practical importance across diverse fields, including medicine, industry, and agriculture areas, which we have briefly outlined in this account.

Keywords

Cyanamide - Oxidation reactions - Chlorination reactions - N-tert-butyl-N-chlorocyanamide - Hydantoin and its analogs

Publication History

Received: 11 August 2025

Accepted after revision: 14 September 2025

Article published online:
18 November 2025

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