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Year 2007, Month 10 (Section Full Articles, Page 2074)

Nitropyrazoles 13. Synthesis and reactivity of 1-methyl-3,5-dinitropyrazole-4-carbonitrile. Site of nucleophilic displacement of the nitro group in 4-R-1-methyl-3,5-dinitropyrazoles

A. A. Zaitsev, T. I. Cherkasova, I. L. Dalinger, V. V. Kachala, Yu. A. Strelenko, I. V. Fedyanin, V. N. Solkan, T. K. Shkineva, G. P. Popova, and S. A. Shevelev

A method for the synthesis of 1-methyl-3,5-dinitropyrazole-4-carbonitrile from 1,4-dimethyl-3,5-dinitropyrazole was developed. Nucleophilic substitution in 1,4-dimethyl-3,5dinitropyrazole, 1-methyl-3,5-dinitropyrazole-4-carboxamide, and 1-methyl-3,5-dinitropyrazole-4-carbonitrile involves solely the 5-NO₂-group in the ring. 1-Methyl-3,5-dinitropyrazole-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 explanation for the regiospecificity of the nucleophilic substitution of the 5-NO₂ group in 4-R-1-methyl-3,5-dinitropyrazoles is given.

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