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Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive

Ruslan Zamil'evich Gilmanov 1
Ruslan Zamil'evich Gilmanov
, 
Valeriy Grigorievich Nikitin 1
Valeriy Grigorievich Nikitin
, 
Farit Garafutdinovich Khayrutdinov 1
Farit Garafutdinovich Khayrutdinov
, 
Kirill Vladimirovich Strizhenko 2
Kirill Vladimirovich Strizhenko
, 
Kirill Yu Suponitsky 3
Kirill Yu Suponitsky
, 
Aleksei Borisovich Sheremetev 2
Aleksei Borisovich Sheremetev
10.1016/j.mencom.2022.01.037
Published 2022-01-03
Communication , Volume 32, Issue 1, 114-116
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Gilmanov R. Z. et al. Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 114-116.
GOST all authors (up to 50) Copy
Gilmanov R. Z., Nikitin V. G., Khayrutdinov F. G., Strizhenko K. V., Suponitsky K. Yu., Sheremetev A. B. Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive // Mendeleev Communications. 2022. Vol. 32. No. 1. pp. 114-116.
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TY - JOUR
DO - 10.1016/j.mencom.2022.01.037
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.037
TI - Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive
T2 - Mendeleev Communications
AU - Gilmanov, Ruslan Zamil'evich
AU - Nikitin, Valeriy Grigorievich
AU - Khayrutdinov, Farit Garafutdinovich
AU - Strizhenko, Kirill Vladimirovich
AU - Suponitsky, Kirill Yu
AU - Sheremetev, Aleksei Borisovich
PY - 2022
DA - 2022/01/03
PB - Mendeleev Communications
SP - 114-116
IS - 1
VL - 32
ER -
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@article{2022_Gilmanov,
author = {Ruslan Zamil'evich Gilmanov and Valeriy Grigorievich Nikitin and Farit Garafutdinovich Khayrutdinov and Kirill Vladimirovich Strizhenko and Kirill Yu Suponitsky and Aleksei Borisovich Sheremetev},
title = {Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.037},
number = {1},
pages = {114--116},
doi = {10.1016/j.mencom.2022.01.037}
}
MLA
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MLA Copy
Gilmanov, Ruslan Zamil'evich, et al. “Bis(furazano)pyridinone N,N'-dioxide: a new high-density insensitive explosive.” Mendeleev Communications, vol. 32, no. 1, Jan. 2022, pp. 114-116. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.01.037.

Keywords

cascade reaction
energetic compound
furazan
furoxan
fused pyridine

Abstract

The synthesis and properties of novel high-dense energetic material based on new 4H,8H-bis(furazano)[3,4-b:3',4'-e]-pyridine ring system are described. An operationally simple, efficient and scalable protocol towards 4H,8H-bis(furazano)-[3,4-b:3',4'-e]pyridin-8-one 1,7-dioxide from commercially available 4-amino-2,6-dichloropyridine in three steps, namely, nitration–azidation–cascade ring closure, has been developed.

References

1.
Pyrido-2,3-furoxane1
Boyer J.H., McCane D.I., McCarville W.J., Tweedie A.T.
Journal of the American Chemical Society, 1953
3.
(a) L. I. Khmel’nitskii, S. S. Novikov and T. I. Godovikova, Khimiya furoksanov: stroenie i sintez (Chemistry of Furoxans: Structure and Synthesis), 2nd edn., Nauka, Moscow, 1996 (in Russian); (b) L. Türker and S. Varis¸, Polycyclic Aromat. Compd., 2009, 29, 228; (c) E. A. Chugunova, A. S. Gazizov, A. R. Burilov, L. M. Yusupova, M. A. Pudovik and O. G. Sinyashin, Russ. Chem. Bull., Int. Ed., 2019, 68, 887 (Izv. Akad. Nauk, Ser. Khim., 2019, 887).
5.
Energetic materials based on poly furazan and furoxan structures
Zhang J., Zhou J., Bi F., Wang B.
Chinese Chemical Letters, 2020
6.
Zlotin S.G., Churakov A.M., Egorov M.P., Fershtat L.L., Klenov M.S., Kuchurov I.V., Makhova N.N., Smirnov G.A., Tomilov Y.V., Tartakovsky V.A.
Mendeleev Communications, 2021
8.
(a) I. B. Starchenkov and V. G. Andrianov, Chem. Heterocycl. Compd., 1996, 32, 618 (Khim. Geterotsikl. Soedin., 1996, 717); (b) A. B. Sheremetev and I. L. Yudin, Mendeleev Commun., 1996, 6, 247; (c) B. B. Averkiev, A. A. Korlyukov, M. Yu. Antipin, A. B. Sheremetev and T. V. Timofeeva, Cryst. Growth Des., 2014, 14, 5418; (d) D. B. Lempert, A. I. Kazakov, A. B. Sheremetev, A. G. Gladyshkin, A. V. Nabatova and L. S. Yanovskii, Russ. Chem. Bull., Int. Ed., 2019, 68, 1856 (Izv. Akad. Nauk, Ser. Khim., 2019, 1856).
9.
(a) A. A. Astrat’ev, D. V. Dashko and A. I. Stepanov, Cent. Eur. J. Chem., 2012, 10, 1087; (b) S. M. Aldoshin, D. B. Lempert, T. K. Goncharov, A. I. Kazakov, S. I. Soglasnova, E. M. Dorofeenko and N. A. Plishkin, Russ. Chem. Bull., Int. Ed., 2016, 65, 2018 (Izv. Akad. Nauk, Ser. Khim., 2016, 2018); (c) Z. G. Aliev, T. K. Goncharov, D. V. Dashko, E. L. Ignat’eva, A. A. Vasil’eva, N. I. Shishov, D. V. Korchagin, Yu. M. Milekhin and S. M. Aldoshin, Russ. Chem. Bull., Int. Ed., 2017, 66, 694 (Izv. Akad. Nauk, Ser. Khim., 2017, 694); (d) D. B. Lempert, V. V. Raznoschikov and L. S. Yanovskiy, Russ. J. Appl. Chem., 2019, 92, 1690 (Zh. Prikl. Khim., 2019, 92, 1578).
10.
Sheremetev A.B., Kulagina V.O., Yudin I.L., Kuzmina N.E.
Mendeleev Communications, 2001
11.
(b) I. N. Zyuzin, K. Yu. Suponitsky and A. B. Sheremetev, J. Heterocycl. Chem., 2012, 49, 561
16.
Polycyclic N-oxides: high performing, low sensitivity energetic materials
Snyder C.J., Wells L.A., Chavez D.E., Imler G.H., Parrish D.A.
Chemical Communications, 2019
17.
(a) A. I. Stepanov, A. A. Astrat’ev, D. V. Dashko, N. P. Spiridonova, S. F. Mel’nikova and I. V. Tselinskii, Russ. Chem. Bull., Int. Ed., 2012, 61, 1024 (Izv. Akad. Nauk, Ser. Khim., 2012, 1019); (b) A. I. Stepanov, D. V. Dashko and A. A. Astrat’ev, Chem. Heterocycl. Compd., 2013, 49, 1068; (c) B.-H. Duan, N. Liu, B. Wang, X. Lu, H. Mo, M. Xu and Y. Shu, Chin. J. Explos. Propellants, 2019, 42, 114, doi: 10.14077/j. issn.1007-7812.2019.02.002; (d) A. I. Kazakov, D. B. Lempert, A. V. Nabatova, D. V. Dashko, V. V. Raznoschikov, L. S. Yanovskii and S. M. Aldoshin, Russ. J. Appl. Chem., 2019, 92, 1696 (Zh. Prikl. Khim., 2019, 92, 1657); (e) L. Zhai, F. Bi, H. Huo, Y. Luo, X. Li, S. Chen and B. Wang, Front. Chem., 2019, 7, doi.org/10.3389/fchem.2019.00559; (f) D. B. Lempert, A. I. Kazakov, A. V. Nabatova, D. V. Dashko, A. I. Stepanov, G. V. Shilov and S. M. Aldoshin, Combust., Explos. Shock Waves, 2020, 56, 621 [Fiz. Goreniya Vzryva, 2020, 56 (6), 3]. (g) N. Liu, C. Xiao, B. Duan, X. Lu, B. Wang, J. Zhang and Q.-L. Yan, ACS Appl. Energy Mater., 2020, 7129.
21.
213. Nitration products of 5-aminoacridine, and the synthesis of 1 : 5- and 4 : 5-diaminoacridine
Hampton A., Magrath D.
Journal of the Chemical Society (Resumed), 1949
22.
(b) K. H. Oh, J. G. Kim and J. K. Park, Org. Lett., 2017, 19, 3994.
23.
Bipyrazole bearing ten nitro groups – a novel highly dense oxidizer for forward-looking rocket propulsions
Dalinger I.L., Suponitsky K.Y., Shkineva T.K., Lempert D.B., Sheremetev A.B.
Journal of Materials Chemistry A, 2018
24.
N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design
Palysaeva N.V., Gladyshkin A.G., Vatsadze I.A., Suponitsky K.Y., Dmitriev D.E., Sheremetev A.B.
Organic Chemistry Frontiers, 2019
25.
3,4‐Dinitrofurazan: Structural Nonequivalence of ortho ‐Nitro Groups as a Key Feature of the Crystal Structure and Density
Suponitsky K.Y., Smol'yakov A.F., Ananyev I.V., Khakhalev A.V., Gidaspov A.A., Sheremetev A.B.
ChemistrySelect, 2020
26.
3-Nitro-1,2,4-triazol-5-one (NTO): High Explosive Insensitive Energetic Material
Sirach R.R., Dave P.N.
Chemistry of Heterocyclic Compounds, 2021
27.
Fizika Vzryva (Physics of Explosion), ed. L. P. Orlenko, 3rd edn., Fizmatlit, Moscow, 2002, vol. 1 (in Russian).