1-Substituted 5-Aminotetrazoles: Syntheses from CNN3 with Primary Amines

1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate gave 1-substituted aminotetrazole in good yield. This protocol also was utilized in the syntheses of bis- and tris(1-substituted 5-aminotetrazole) derivatives.