Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Abstract

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan­amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

An Efficient Promising Direction for the Synthesis of Dispirotripiperazine (6-6-6 DSTP) Core

“…Cyanogen bromide (BrCN) is the class of important compounds widely used in von Braun degradation 15 and useful for the cleavage of carbon-heteroatom bonds. The BrCN provides a convenient method for the demethylation of tertiary methylamines 16 in which a dialkyl-substituted cyanamide 17,18 and an alkyl bromide were formed, with bromide attack occurring at the more electrophilic or sterically accessible site. The BrCN can also cleavage the thioethers, for example, methionine cleavage in peptide chains.…”