Synthesis of 5-(3, 3-disubstituted-1-triazenyl) imidazole-4-carbonitriles

The 3, 3-dimethyl-, 3-n-butyl-3-methyl-, 3-(2-hydroxyethyl)-3-methyl-, 3,3-bis(2-fluoroethyl)-, and 3, 3-bis(2-chloroethyl)-1-triazenyl derivatives of imidazole-4-carbonitrile were prepared from 5-diazoimidazole-4-carbonitrile, a stable compound which produced a mass spectrum consistent with its structure. In contrast to the corresponding carboxamides, none of the triazenylimidazole-4-carbonitriles were active against lymphatic leukemia L-1210 im mice. Like the analogous carboxamide, the bis(2-chloroethyl) triazene readily cyclizes to the 1, 2, 3-triazolinium chloride.