Treatment of certain diaminomethylenehydrazones 1 of aromatic carbonyl compounds with ethyl N‐cyanoimidate (2) in acetonitrile in the presence of a tertiary amine at room temperature gives the corresponding amino(N‐cyanoiminomethyl)aminomethylenehydrazones 3 in high yields. The intermediate 3 can readily be cyclized to the corresponding 5‐amino‐2,3‐dihydro[1,2,4]triazolo[1,5‐a][1,3,5]triazines 4 in moderate to good yields by brief heating in acetonitrile. When the reaction of diaminomethylenehydrazones 1 with ethyl N‐cyanoimidate (2) is performed at reflux temperature in the presence of a tertiary amine, 5‐amino‐2,3‐dihydro[1,2,4]triazolo[1,5‐a]1,3,5]triazines 4 can be directly obtained in moderate yields. The yields of triazolotriazine produced by the one‐step synthesis are generally comparable or even higher than the overall yields from the two‐step procedure.
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