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For the first time pyrazole containing three nitro groups in the pyrazole cycle, viz., 1,3,4 tri nitropyrazole, was obtained by N nitration of 3,4 dinitropyrazole. 1,3,4 Trinitropyrazole enters the cine substitution reaction of N nitro group under the action of O , N , and C nucleophyls under mild conditions. Thus, general method of synthesis of 5 substituted 3,4 dinitropyrazoles containing free NH fragment was worked out.

A method for the synthesis of 1 methyl 3,5 dinitropyrazole 4 carbonitrile from 1,4 di methyl 3,5 dinitropyrazole was developed. Nucleophilic substitution in 1,4 dimethyl 3,5 dinitropyrazole, 1 methyl 3,5 dinitropyrazole 4 carboxamide, and 1 methyl 3,5 dinitro pyrazole 4 carbonitrile involves solely the 5 NO 2 group in the ring. 1 Methyl 3,5 dinitro pyrazole 4 carbonitrile reacts with thioglycolic acid phenylamide and potassium carbonate to give 4 amino 1 methyl 3 nitro N phenyl 1H thieno[2,3 c]pyrazole 5 carboxamide. The use of glycolic acid phenylamide instead of thioglycolic acid N phenylamide under analogous conditions resulted in 5 anilino 1 methyl 3 nitro 1H pyrazole 4 carbonitrile. An explana tion for the regiospecificity of the nucleophilic substitution of the 5 NO 2 group in 4 R 1 methyl 3,5 dinitropyrazoles is given.

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