An alternative synthesis of 7-amino-6-nitro-substituted azolo[1,5-a]pyrimidines

New 7-amino-6-nitro-substituted [1,2,4]triazolo- and pyrazolo[1,5-a]pyrimidines were synthesized by an alternative strategy based on amino azoles and 2-nitro-3-(p-tolylamino)acrylonitrile. Unexpectedly, 3,5-dinitro-N-(p-tolyl)pyridine-2,6-diamine was formed when the starting 5-amino-1,2,4-triazoles contained NO₂ or CF₃ substituents.