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Mendeleev Communications, 2022, Volume 32, Issue 6, Pages 703–713
DOI: https://doi.org/10.1016/j.mencom.2022.11.001
(Mi mendc774)
 

This article is cited in 32 scientific papers (total in 32 papers)

Focus Article

Energetic heterocyclic N-oxides: synthesis and performance

A. A. Larin, L. L. Fershtat

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Novel synthetic strategies toward construction and functionalization of nitrogen-rich energetic compounds bearing at least one heterocyclic N-oxide scaffold are briefly overviewed. The present focus review summarizes main recent advances (published in the period 2017–2022) in the chemistry of five- and six-membered heterocyclic N-oxides as well as their linear combinations and fused bi-, tri- and tetraheterocyclic frameworks which are of paramount importance for the development of next-generation energetic materials. Physicochemical properties along with detonation performance and mechanical sensitivities of the reported high-energy substances are discussed and their application potential is especially emphasized.
Keywords: energetic materials, nitrogen heterocycles, fused heterocycles, detonation performance, N-oxides, synthetic methodologies.
Document Type: Article
Language: English


Citation: A. A. Larin, L. L. Fershtat, “Energetic heterocyclic N-oxides: synthesis and performance”, Mendeleev Commun., 32:6 (2022), 703–713
Linking options:
  • https://www.mathnet.ru/eng/mendc774
  • https://www.mathnet.ru/eng/mendc/v32/i6/p703
  • This publication is cited in the following 32 articles:
    1. Victor P. Zelenov, Ivan V. Fedyanin, Aida I. Samigullina, Alexandr A. Larin, Aleksei B. Sheremetev, “R-Substituent vs. exocyclic oxygen: influence on synthesis and crystal packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides”, CrystEngComm, 2025  crossref
    2. Galina A. Gazieva, Yulia B. Evdokimenkova, Natalya O. Soboleva, Advances in Heterocyclic Chemistry, 2025  crossref
    3. Erin N. Groneck, Nathan Peek, Will E. Lynch, Clifford W. Padgett, “Crystal structures of zinc(II) coordination complexes with isoquinoline N-oxide”, Acta Crystallogr E Cryst Commun, 81:2 (2025), 132  crossref
    4. Yuteng Cao, Tianyu Jiang, Shiluo Chen, Honglei Xia, Yu Liu, Wenquan Zhang, “Driving the efficient construction and functional-group editing of 2-(1,2,4-triazole-5-yl)-1,3,4-oxadiazole-based high-energy compounds by a resonance-assisted hydrogen bonding strategy”, J. Mater. Chem. A, 2025  crossref
    5. M. P. Egorov, V. P. Ananikov, E. G. Baskir, S. E. Boganov, V. I. Bogdan, A. N. Vereshchagin, V. A. Vil', I. L. Dalinger, A. D. Dilman, O. L. Eliseev, S. G. Zlotin, E. A. Knyazeva, V. M. Kogan, L. O. Kononov, M. M. Krayushkin, V. B. Krylov, L. M. Kustov, V. V. Levin, B. V. Lichitsky, M. G. Medvedev, N. E. Nifantiev, O. A. Rakitin, A. M. Sakharov, I. V. Svitanko, G. A. Smirnov, A. Yu. Stakheev, M. A. Syroeshkin, A. O. Terent'ev, Yu. V. Tomilov, E. V. Tretyakov, I. V. Trushkov, L. L. Fershtat, V. A. Chaliy, V. Z. Shirinian, “Current trends in organic chemistry: contribution of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences”, Russ Chem Bull, 73:9 (2024), 2423  crossref
    6. Nikita V. Muravyev, Leonid Fershtat, Qinghua Zhang, “Synthesis, design and development of energetic materials: Quo Vadis?”, Chemical Engineering Journal, 486 (2024), 150410  crossref
    7. D. M. Bystrov, L. L. Fershtat, “Reactivity of 2-aminopyridine N-oxides”, Russ Chem Bull, 73:1 (2024), 33  crossref
    8. Alexander A. Larin, Ekaterina V. Dubasova, Ivan V. Ananyev, Konstantin A. Monogarov, Galina A. Gazieva, Leonid L. Fershtat, “New energetic 1,2,4‐triazole‐nitrofuroxan hybrids”, Journal of Heterocyclic Chem, 61:5 (2024), 713  crossref
    9. Jiarong Zhang, Huan Huo, Lianjie Zhai, Fuqiang Bi, Bozhou Wang, “Research progress on the synthesis of energetic N-oxides based on diazine, triazine and tetrazine”, FirePhysChem, 2024  crossref
    10. N. V. Lobanov, A. N. Rykov, A. V. Stepanova, A. A. Larin, L. L. Fershtat, I. F. Shishkov, “Equilibrium Molecular Structure of 3-Cyano-4-Amino-1,2,5-Oxadiazole-2-Oxide in the Gas Phase”, J Struct Chem, 65:8 (2024), 1603  crossref
    11. N. V. Lobanov, A. N. Rykov, A. V. Stepanova, D. A. Kalugin, A. A. Larin, L. L. Fershtat, I. F. Shishkov, “Molecular structure of 3-cyano-4-azido-1,2,5-oxadiazole 2-oxide studied by means of gas electron diffraction and quantum chemical calculations”, Struct Chem, 2024  crossref
    12. Yuteng Cao, Tianyu Jiang, Ying Li, Honglei Xia, Yu Liu, Wenquan Zhang, “Simple synthesis of monocyclic pyrimidine-based energetic molecule with “amino–nitro–hydrazino” arrangement”, FirePhysChem, 2024  crossref
    13. D.V. Khakimov, T.S. Pivina, “New potential HEDMs with a pyridazine core: Structural modeling and assessment of thermochemical properties”, FirePhysChem, 4:1 (2024), 42  crossref
    14. Sid Ahmed Kaas, Fayssal Triki Baara, Youcef Megrouss, Salem Yahiaoui, Ahmed Djafri, Fatima Zohra Boudjenane, Abdelkader Chouaih, Ayada Djafri, Antonis Hatzidimitriou, “Synthesis, crystal structure, Hirshfeld surface analysis, computational investigations and molecular docking studies of (Z)-3-N-(methyl)-2-N'-(4-methoxyphenylimino) thiazolidin-4-one dihydrate”, Journal of Molecular Structure, 1308 (2024), 137964  crossref
    15. Dmitry B. Vinogradov, Leonid L. Fershtat, “Energetic azine N-oxides: State-of-the-art achievements in the synthesis and performance”, Chemical Engineering Journal, 2024, 158859  crossref
    16. V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125  mathnet  mathnet  crossref  isi  scopus
    17. E. E. Vinogradova, A. A. Larin, G. A. Gazieva, “Synthesis of hybrid molecules based on thioglycolurils and 1,2,5-oxadiazoles via the Eschenmoser sulfide contraction”, Mendeleev Commun., 34:1 (2024), 122–125  mathnet  crossref
    18. A. V. Shaferov, L. L. Fershtat, “Energetic 1,2,4-oxadiazoles: synthesis and properties”, Russian Chem. Reviews, 93:2 (2024), RCR5109  mathnet  mathnet  crossref  isi  scopus
    19. S. P. Balabanova, A. A. Voronin, A. M. Churakov, M. S. Klenov, I. V. Fedyanin, Yu. A. Strelenko, V. A. Tartakovsky, “A new conjugated tripoid N4 system containing furazan and triazolofurazan cores linked by a nitrogen bridge”, Mendeleev Commun., 34:6 (2024), 862–864  mathnet  crossref
    20. Alexander V. Shaferov, Sergey T. Arakelov, Fedor E. Teslenko, Alla N. Pivkina, Nikita V. Muravyev, Leonid L. Fershtat, “First Example of 1,2,5‐Oxadiazole‐Based Hypergolic Ionic Liquids: A New Class of Potential Energetic Fuels”, Chemistry A European J, 29:44 (2023)  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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