Triazines and related products. Part 30. Cationic analogues of the antitumour drug 2,4,6-tris(dimethylamino)-1,3,5-triazine (hexamethylmelamine)

Abstract

Chloro-1,3,5-triazines react with trimethylamine in ether to afford water-soluble quaternary salts. 2,4,6-Tris(dimethylamino)-1,3,5-oxadiazinium chloride (10) is formed when dimethylcyanamide and dimethylcarbamoyl chloride are heated at 170 °C. The oxadiazinium chloride reacts with ammonia to afford 2,4-bis(dimethylamino)-1,3,5-triazin-6(1H)-one by an ANRORC reaction, with primary amines to afford amine-adducts (15) of the 1,3,5-oxadiazine or, under forcing conditions, 1,2,4-trisubstituted-1,3,5-triazin-6(1H)-ones (20), (21) or (22). None of the cationic salts displayed antitumour activity in vivo in tumour-bearing mice and they were poor substrates for oxidative metabolism in vitro.