Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative
Igor L Dalinger
1
,
Irina A. Vatsadze
1
,
Tatyana K Shkineva
1
,
Galina P Popova
1
,
Svyatoslav A. Shevelev
1
,
Publication type: Journal Article
Publication date: 2013-07-02
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
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.
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Total citations:
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Citations from 2025:
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(14.58%)
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GOST
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Dalinger I. L. et al. Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative // Journal of Heterocyclic Chemistry. 2013. Vol. 50. No. 4. pp. 911-924.
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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. Vol. 50. No. 4. pp. 911-924.
Cite this
RIS
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TY - JOUR
DO - 10.1002/jhet.1026
UR - https://doi.org/10.1002/jhet.1026
TI - Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative
T2 - Journal of Heterocyclic Chemistry
AU - Dalinger, Igor L
AU - Vatsadze, Irina A.
AU - Shkineva, Tatyana K
AU - Popova, Galina P
AU - Shevelev, Svyatoslav A.
AU - Nelyubina, Yuliya V.
PY - 2013
DA - 2013/07/02
PB - Wiley
SP - 911-924
IS - 4
VL - 50
SN - 0022-152X
SN - 1943-5193
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Dalinger,
author = {Igor L Dalinger and Irina A. Vatsadze and Tatyana K Shkineva and Galina P Popova and Svyatoslav A. Shevelev and Yuliya V. Nelyubina},
title = {Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative},
journal = {Journal of Heterocyclic Chemistry},
year = {2013},
volume = {50},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/jhet.1026},
number = {4},
pages = {911--924},
doi = {10.1002/jhet.1026}
}
Cite this
MLA
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Dalinger, Igor L., et al. “Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative.” Journal of Heterocyclic Chemistry, vol. 50, no. 4, Jul. 2013, pp. 911-924. https://doi.org/10.1002/jhet.1026.
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