The reaction of cyanogen bromide (1) with primary amines (2a-p), including arylmethylamines (2l-p), gave the corresponding cyanamides (3a-p). Trimerization of 3a-p gave 1, 3, 5-trisubstituted 2, 4, 6-triiminohexahydro-1, 3, 5-triazines (isomelamines)(4a-p), which were treated with hydrochloric acid to give the corresponding 1, 3, 5-trisubstituted 2, 4, 6-trioxohexahydro-1, 3, 5-triazines (isocyanurates)(5a-c, f) and 1, 3, 5-trisubstituted 2- ...
[D'Silva, Themistocles D. J.; Lopes, Anibal; Jones, Russell L.; Singhawangcha, Sureerat; Chan, John K. Journal of Organic Chemistry, 1986 , vol. 51, # 20 p. 3781 - 3788]