2-Nitroguanidine reacts with dicarboxylic acid dihydrazides to form intermediate condensation product which undergoes intramolecular cyclization, yielding the corresponding bis(3-nitroamino-1,2,4-triazol-5-yl)alkanes and 5,5'-bi(3-nitroamino-1,2,4-triazole) potassium salt. The structure of the products was confirmed by comparing their electron absorption spectra with those of 3,5-bis(nitroamino)-1,2,4-triazole salts.* For communication VI, see [1].
A new procedure for the synthesis of 5(3)-nitroamino-1,2,4-triazole-3(5)-carboxylic acid and 5,5'-bi(3-nitroamino-1,2,4-triazole) potassium salt has been developed. It includes cyclization of [2-(N 2 -nitrocarbamimidoyl)hydrazino]oxoacetic acid and 2,2'-bis(N 2 -nitrocarbamimidoyl)oxalohydrazide, respectively, which are prepared by reaction of 1-amino-2-nitroguanidine with oxalic acid. The reaction of 5(3)-nitroamino-1,2,4-triazole-3(5)-carbohydrazide with 1-methyl-2-nitro-1-nitrosoguanidine leads to N'-(N 2 -nitrocarbamimidoyl)-5(3)-nitroamino-1,2,4-triazole-3(5)-carbohydrazide whose intramolecular cyclization in the presence of bases may be regarded as a new method of synthesis of 5,5'-bi(3-nitroamino-1,2,4-triazole) salts. Scheme 1.
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