Home / Publications / Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles

Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles

Tigran E Khoranyan 1
Tigran E Khoranyan
Alexander Vasilyvich Kormanov 1
Alexander Vasilyvich Kormanov
Alevtina Nikolaevna Pivkina 2
Alevtina Nikolaevna Pivkina
Kirill Yu Suponitsky 1
Kirill Yu Suponitsky
Igor L'vovich Dalinger 1
Igor L'vovich Dalinger
2 N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
Published 2025-03-31
CommunicationVolume 35, Issue 3, 249-251
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Khoranyan T. E. et al. Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles // Mendeleev Communications. 2025. Vol. 35. No. 3. pp. 249-251.
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Khoranyan T. E., Kormanov A. V., Pivkina A. N., Suponitsky K. Yu., Dalinger I. L. Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles // Mendeleev Communications. 2025. Vol. 35. No. 3. pp. 249-251.
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TY - JOUR
DO - 10.71267/mencom.7628
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7628
TI - Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles
T2 - Mendeleev Communications
AU - Khoranyan, Tigran E
AU - Kormanov, Alexander Vasilyvich
AU - Pivkina, Alevtina Nikolaevna
AU - Suponitsky, Kirill Yu
AU - Dalinger, Igor L'vovich
PY - 2025
DA - 2025/03/31
PB - Mendeleev Communications
SP - 249-251
IS - 3
VL - 35
ER -
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@article{2025_Khoranyan,
author = {Tigran E Khoranyan and Alexander Vasilyvich Kormanov and Alevtina Nikolaevna Pivkina and Kirill Yu Suponitsky and Igor L'vovich Dalinger},
title = {Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7628},
number = {3},
pages = {249--251},
doi = {10.71267/mencom.7628}
}
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Khoranyan, Tigran E., et al. “Unusual formation of 4-diazo-3-nitriminopyrazoles upon acid nitration of pyrazolo[3,4-d][1,2,3]triazoles.” Mendeleev Communications, vol. 35, no. 3, Mar. 2025, pp. 249-251. https://mendcomm.colab.ws/publications/10.71267/mencom.7628.

Keywords

1,2,3-triazoles
differential scanning calorimetry
energetic properties
nitration
pyrazoles
pyrazolo[3,4-d][1,2,3]triazoles
ring opening
X-ray diffraction analysis

Abstract

Nitration of 6-R-4-phenylpyrazolo[3,4-d][1,2,3]triazoles at the phenyl substituent is accompanied by the triazole ring opening to give new 3-R-4-diazo-1-(di)nitrophenylpyrazole- 5-nitrimines. Chemical and physicochemical properties of the prepared compounds are reported.

References

1.
Nitro compounds as the core structures of promising energetic materials and versatile reagents for organic synthesis
Zlotin S.G., Dalinger I.L., Makhova N.N., Tartakovsky V.A.
Russian Chemical Reviews, 2020
2.
Sensitivity of energetic materials: Evidence of thermodynamic factor on a large array of CHNOFCl compounds
Muravyev N.V., Meerov D.B., Monogarov K.A., Melnikov I.N., Kosareva E.K., Fershtat L.L., Sheremetev A.B., Dalinger I.L., Fomenkov I.V., Pivkina A.N.
Chemical Engineering Journal, 2021
3.
Crystal structure refinement withSHELXL
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry, 2015
4.
4,4′-Bis(nitramino)azofurazan and its salts. Study of molecular and crystal structure based on X-ray and quantum chemical data
Suponitsky K.Y., Lyssenko K.A., Antipin M.Y., Aleksandrova N.S., Sheremetev A.B., Novikova T.S.
Russian Chemical Bulletin, 2009
5.
Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles
Horneff T., Chuprakov S., Chernyak N., Gevorgyan V., Fokin V.V.
Journal of the American Chemical Society, 2008
6.
Rh-Catalyzed Transannulation of Pyridotriazoles with Alkynes and Nitriles
Chuprakov S., Hwang F., Gevorgyan V.
Angewandte Chemie - International Edition, 2007
7.
Synthesis of 1,2,3,4-Tetrazine 1,3-Dioxides Annulated with 1(2)-Aryl-1,2,3-triazoles
Voronin A.A., Churakov A.M., Klenov M.S., Strelenko Y.A., Fedyanin I.V., Tartakovsky V.A.
European Journal of Organic Chemistry, 2017
8.
Asymmetric N,N′-ethylene-bridged azole-based compounds: Two way control of the energetic properties of compounds
Kumar D., Mitchell L.A., Parrish D.A., Shreeve J.M.
Journal of Materials Chemistry A, 2016
9.
EnergeticN,N′-Ethylene-Bridged Bis(nitropyrazoles): Diversified Functionalities and Properties
Yin P., Zhang J., Parrish D.A., Shreeve J.M.
Chemistry - A European Journal, 2014
10.
1,2,4‐Triazole Links and N ‐Azo Bridges Yield Energetic Compounds
Tang Y., Gao H., Parrish D.A., Shreeve J.M.
Chemistry - A European Journal, 2015
11.
4-Chloro-3,5-dinitropyrazole: a precursor for promising insensitive energetic compounds
He C., Zhang J., Parrish D.A., Shreeve J.M.
Journal of Materials Chemistry A, 2013
12.
Fused heterocycle-based energetic salts: alliance of pyrazole and 1,2,3-triazole
Yin P., He C., Shreeve J.M.
Journal of Materials Chemistry A, 2016
13.
Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
Fischer D., Gottfried J.L., Klapötke T.M., Karaghiosoff K., Stierstorfer J., Witkowski T.G.
Angewandte Chemie, 2016
14.
Fused heterocycle-based energetic materials (2012–2019)
Gao H., Zhang Q., Shreeve J.M.
Journal of Materials Chemistry A, 2020
16.
Learning to fly: thermochemistry of energetic materials by modified thermogravimetric analysis and highly accurate quantum chemical calculations.
Muravyev N.V., Monogarov K.A., Melnikov I.N., Pivkina A.N., Kiselev V.G.
Physical Chemistry Chemical Physics, 2021
17.
Dinitropyrazoles
Zaitsev A.A., Dalinger I.L., Shevelev S.A.
Russian Chemical Reviews, 2009
21.
Progress and performance of energetic materials: open dataset, tool, and implications for synthesis
Muravyev N.V., Wozniak D.R., Piercey D.G.
Journal of Materials Chemistry A, 2022
22.
From Pyrazolones to Azaindoles: Evolution of Active-Site SHP2 Inhibitors Based on Scaffold Hopping and Bioisosteric Replacement
Mostinski Y., Heynen G.J., López-Alberca M.P., Paul J., Miksche S., Radetzki S., Schaller D., Shanina E., Seyffarth C., Kolomeets Y., Ziebart N., de Schryver J., Oestreich S., Neuenschwander M., Roske Y., et. al.
Journal of Medicinal Chemistry, 2020
24.
Toward Chemical Accuracy in Predicting Enthalpies of Formation with General-Purpose Data-Driven Methods
Zheng P., Yang W., Wu W., Isayev O., Dral P.O.
Journal of Physical Chemistry Letters, 2022
26.
3-(4-R-3-Furazanyl)-5-nitropyrazolyl-1,2,4-oxadiazoles as a new class of energy rich ensembles
Khoranyan T.E., Serushkina O.V., Vatsadze I.A., Suponitsky K.Y., Monogarov K.A., Shkineva T.K., Dalinger I.L.
Russian Chemical Bulletin, 2022
27.
Synthesis of 2,5-disubstituted pyrazolyl-1,3,4-oxadiazoles by the Huisgen reaction
Shkineva T.K., Serushkina O.V., Vatsadze I.A., Khoranyan T.E., Dalinger I.L.
Russian Chemical Bulletin, 2022
28.
Constructing fused N-heterocycles from unprotected mesoionic N-heterocyclic olefins and organic azides via diazo transfer
Liang Q., Hayashi K., Zeng Y., Jimenez-Santiago J.L., Song D.
Chemical Communications, 2021
29.
Regioisomeric 3,5-di(nitropyrazolyl)-1,2,4-oxadiazoles and their energetic properties
Khoranyan T.E., Shkineva T.K., Vatsadze I.A., Shakhnes A.K., Muravyev N.V., Sheremetev A.B., Dalinger I.L.
Chemistry of Heterocyclic Compounds, 2022
31.
Novel energetic CNO oxidizer: Pernitro-substituted pyrazolyl-furazan framework
Dalinger I.L., Shkineva T.K., Vatsadze I.A., Kormanov A.V., Kozeev A.M., Suponitsky K.Y., Pivkina A.N., Sheremetev A.B.
FirePhysChem, 2021
35.
Synthesis of 2-hetaryl-6H-pyrazolo[3,4-d]-1,2,3-triazoles
Rangnekar D.W., Dhamnaskar S.V.
Journal of Heterocyclic Chemistry, 1988
36.
Synthesis and Biological Evaluation of a Series of Substituted Pyrazolo[3,4-d]-1,2,3-triazoles and Pyrazolo[3,4-d]oxazoles
Vicentini C.B., Manfredini S., Manfrini M., Bazzanini R., Musiu C., Putzolu M., Perra G., Marongiu M.E.
Archiv der Pharmazie, 1998
38.
A Synthetic Entry to 1- and 2-Aminopyrazolo[3,4-d]-1,2,3-triazoles
Giori P., B. Vicentini C., Ferretti V., C. Veronese A.
Heterocycles, 1995
39.
Pyrazolo-triazoles as light activable dna cleaving agents
Manfredini S., Beatrice Vicentini C., Manfrini M., Bianchi N., Rutigliano C., Mischiati C., Gambari R.
Bioorganic and Medicinal Chemistry, 2000
40.
Luminescence of 1,3,6-trisubstituted pyrazolo[3,4-d][1,2,3]triazoles
Liang Q., Hayashi K., Philippi F., Song D.
Canadian Journal of Chemistry, 2023
44.
N-Acetonylnitropyrazolecarboxylic acids in the selective synthesis of N-acetonyl-3-R-5-nitropyrazolyl-1,2,4-oxadiazoles
Khoranyan T.E., Gushchina P.K., Suponitsky K.Y., Dalinger I.L.
Russian Chemical Bulletin, 2024
45.
The first example of a cine-substitution in a series of 1,3-dinitropyrazoles
Shkineva T.K., Krasnova S.A., Dalinger I.L.
Chemistry of Heterocyclic Compounds, 2024