Heterocyclization of compounds containing diazo and cyano groups. 3. Two pathways in the cyclization of 2-diazo-2-cyanoacetic acid derivatives under the influence of bases

1,2,3-Triazol-5-olates are formed in the reaction of diazomalonodiamide and 2-diazo-2-cyanoacetic acid amide and N-methylamide with sodium ethoxide, triethylamine, and ammonia. The products of the reaction of 2-diazo-2-cyanoacetamide with primary amines are mixtures of 4-cyano-1,2,3-triazol-5-olates and 5-amino-1-alkyl-1,2,3-triazole-4-carboxamides.