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

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 Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2007, Volume: 56, Number: 10, Pages: 2074-2084 Pages count : 11 DOI: 10.1007/s11172-007-0323-6

Authors

Zaitsev A.A. ¹ , Cherkasova T.I. ¹ , Dalinger I.L. ¹ , Kachala V.V. ¹ , Strelenko Yu.A. ¹ , Fedyanin I.V. ² , Solkan V.N. ¹ , Shkineva T.K. ¹ , Popova G.P. ¹ , Shevelev S.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	N. A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

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-3,5-dinitropyrazole, 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.

Zaitsev A.A. , Cherkasova T.I. , Dalinger I.L. , Kachala V.V. , Strelenko Y.A. , Fedyanin I.V. , Solkan V.N. , Shkineva T.K. , Popova G.P. , Shevelev S.A.
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
Russian Chemical Bulletin. 2007. V.56. N10. P.2074-2084. DOI: 10.1007/s11172-007-0323-6 WOS Scopus OpenAlex

≡ Web of science:	WOS:000254206300024
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