Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative

Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative Full article

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Output data

Year: 2013, Volume: 50, Number: 4, Pages: 911-924 Pages count : 14 DOI: 10.1002/jhet.1026

Authors

Dalinger Igor L. ¹ , Vatsadze Irina A. ¹ , Shkineva Tatyana K. ¹ , Popova Galina P. ¹ , Shevelev Svyatoslav A. ¹ , Nelyubina Yuliya V. ²

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky pr., 47, Moscow, Russia
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilov Str., 28, Moscow, Russia

3,4,5-Trinitro-1H-pyrazole (1) has been obtained via nitration of 3,5-dinitropyrazole with mixture of sulfuric and nitric acids. Compound 1 reacts with excess ammonia and aliphatic amines, in the presence of bases with NH-azoles, phenols, thiols, and triflouroethanol at mild conditions in water. All these reactions occur as the nucleophilic substitution of the nitro-group at position 4 in 1 affording 4-R-3,5-dinitropyrazoles. The product of methylation of 1, N-methyl-3,4,5-trinitropyrazole (4), also reacts with thiols, phenols, oximes, ammonia, amines, and NH-azoles. The reactions proceed with high yields but nucleophilic substitutions in these cases occur regioselectively at position 5 in 4 to afford 5-R-3,4-dinitropyrazoles.

Dalinger I.L. , Vatsadze I.A. , Shkineva T.K. , Popova G.P. , Shevelev S.A. , Nelyubina Y.V.
Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative
Journal of Heterocyclic Chemistry. 2013. V.50. N4. P.911-924. DOI: 10.1002/jhet.1026 WOS Scopus OpenAlex

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