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Mendeleev Communications, 1997, Volume 7, Issue 2, Pages 58–59
DOI: https://doi.org/10.1070/MC1997v007n02ABEH000670
(Mi mendc4781)
 

This article is cited in 21 scientific papers (total in 21 papers)

Synthesis of 4-diazo-3,5-dinitropyrazole and characteristic features of its behaviour towards nucleophiles

I. L. Dalinger, T. I. Cherkasova, S. A. Shevelev

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Full-text PDF (77 kB) Citations (21)
Abstract: Diazopyrazole containing two nitro groups in the ring – 4-diazo-3,5-dinitropyrazole – has been synthesised for the first time by diazotisation of the corresponding aminodinitropyrazole. 4-Diazo-3,5-dinitropyrazole reacts with salts of methylene-active compounds, CH2(CN)NO2 and CH2(COCH3)2, to give azo coupling products, whereas its interaction with nucleophiles such as Br, N3 or H2O(H+) involves replacement of one of the nitro groups yielding 4-diazo-3-R-5-nitropyrazoles.
Document Type: Article
Language: English


Citation: I. L. Dalinger, T. I. Cherkasova, S. A. Shevelev, “Synthesis of 4-diazo-3,5-dinitropyrazole and characteristic features of its behaviour towards nucleophiles”, Mendeleev Commun., 7:2 (1997), 58–59
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  • https://www.mathnet.ru/eng/mendc/v7/i2/p58
  • This publication is cited in the following 21 articles:
    1. Prachi Bhatia, Krishna Pandey, Dheeraj Kumar, “Zwitterionic Energetic Materials: Synthesis, Structural Diversity and Energetic Properties”, Chemistry — An Asian Journal, 19:17 (2024)  crossref
    2. Max Born, Konstantin Karaghiosoff, Thomas M. Klapötke, Michael Voggenreiter, “Oxetane Monomers Based On the Powerful Explosive LLM‐116: Improved Performance, Insensitivity, and Thermostability”, ChemPlusChem, 87:3 (2022)  crossref
    3. Sergey Bondarchuk, The 26th International Electronic Conference on Synthetic Organic Chemistry, 2022, 48  crossref
    4. S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, “Nitro compounds as the core structures of promising energetic materials and versatile reagents for organic synthesis”, Russian Chem. Reviews, 89:1 (2020), 1–54  mathnet  mathnet  crossref  isi  scopus
    5. Mao‐Xi Zhang, Philip F. Pagoria, Gregory H. Imler, Damon Parrish, “Trimerization of 4‐Amino‐3,5‐dinitropyrazole: Formation, Preparation, and Characterization of 4‐Diazo‐3,5‐bis(4‐amino‐3,5‐dinitropyrazol‐1‐yl) pyrazole (LLM‐226)”, Journal of Heterocyclic Chem, 56:3 (2019), 781  crossref
    6. Yao Du, Jichuan Zhang, Panpan Peng, Hui Su, Shenghua Li, Siping Pang, “Synthesis and characterization of three pyrazolate inner diazonium salts: green, powerful and stable primary explosives”, New J. Chem., 41:17 (2017), 9244  crossref
    7. V.P. Sinditskii, S.P. Smirnov, V.Yu. Egorshev, A.N. Chernyi, T.K. Shkineva, N.V. Palysaeva, K.Yu. Suponitsky, I.L. Dalinger, “Thermal decomposition peculiarities and combustion behavior of nitropyrazoles”, Thermochimica Acta, 651 (2017), 83  crossref
    8. Laser Ignition of Energetic Materials, 2014, 91  crossref
    9. Ping Yin, Jiaheng Zhang, Damon A. Parrish, Jean'ne M. Shreeve, “Energetic N,N′‐Ethylene‐Bridged Bis(nitropyrazoles): Diversified Functionalities and Properties”, Chemistry A European J, 20:50 (2014), 16529  crossref
    10. Igor L. Dalinger, Irina A. Vatsadze, Tatyana K. Shkineva, Galina P. Popova, Svyatoslav A. Shevelev, Yuliya V. Nelyubina, “Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and ItsN-Methyl Derivative”, J. Heterocyclic Chem., 50:4 (2013), 911  crossref
    11. T. K. Shkineva, I. L. Dalinger, I. A. Vatsadze, A. V. Kormanov, S. A. Shevelev, “Nitropyrazoles 21. Selective nucleophilic substitution of the nitro group in 1-amino-3,4-dinitropyrazole”, Russ Chem Bull, 61:2 (2012), 467  crossref
    12. Yves L. Janin, “Preparation and Chemistry of 3/5-Halogenopyrazoles”, Chem. Rev., 112:7 (2012), 3924  crossref
    13. Grégoire Hervé, Christian Roussel, Hervé Graindorge, “Selective Preparation of 3,4,5‐Trinitro‐1H‐Pyrazole: A Stable All‐Carbon‐Nitrated Arene”, Angewandte Chemie, 122:18 (2010), 3245  crossref
    14. Grégoire Hervé, Christian Roussel, Hervé Graindorge, “Selective Preparation of 3,4,5‐Trinitro‐1H‐Pyrazole: A Stable All‐Carbon‐Nitrated Arene”, Angew Chem Int Ed, 49:18 (2010), 3177  crossref
    15. I. L. Dalinger, I. A. Vatsadse, T. K. Shkineva, G. P. Popova, B. I. Ugrak, S. A. Shevelev, “Nitropyrazoles”, Russ Chem Bull, 59:8 (2010), 1631  crossref
    16. I. L. Dalinger, I. A. Vatsadze, T. K. Shkineva, G. P. Popova, S. A. Shevelev, “The specific reactivity of 3,4,5-trinitro-1H-pyrazole”, Mendeleev Commun., 20:5 (2010), 253–254  mathnet  crossref
    17. A. A. Zaitsev, I. O. Kortusov, I. L. Dalinger, V. V. Kachala, G. P. Popova, S. A. Shevelev, “Nitropyrazoles 16. The use of methoxymethyl group as a protecting group for the synthesis of 4-methyl-3-nitro-5-R-pyrazoles”, Russ Chem Bull, 58:10 (2009), 2118  crossref
    18. L. Yet, Comprehensive Heterocyclic Chemistry III, 2008, 1  crossref
    19. Robert D. Schmidt, Gregory S. Lee, Philip F. Pagoria, Alexander R. Mitchell, Richard Gilardi, “Synthesis of 4‐amino‐3,5‐dinitro‐1H‐pyrazole using vicarious nucleophilic substitution of hydrogen”, Journal of Heterocyclic Chem, 38:5 (2001), 1227  crossref
    20. S. A. Shevelev, I. L. Dalinger, V. I. Gulevskaya, T. I. Cherkasova, V. M. Vinogradov, B. I. Ugrak, A. M. Starosotnikov, “Synthesis of mesoionic 3-aryl(hetaryl)-1,2,3,4-oxatriazol-5-ones b based on N-aryl-and N-hetarylhydrazones of bromonitroformaldehyde”, Chem Heterocycl Compd, 35:3 (1999), 363  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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