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
Linking options:
https://www.mathnet.ru/eng/mendc4781
https://www.mathnet.ru/eng/mendc/v7/i2/p58
This publication is cited in the following 21 articles:
Prachi Bhatia, Krishna Pandey, Dheeraj Kumar, “Zwitterionic Energetic Materials: Synthesis, Structural Diversity and Energetic Properties”, Chemistry — An Asian Journal, 19:17 (2024)
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)
Sergey Bondarchuk, The 26th International Electronic Conference on Synthetic Organic Chemistry, 2022, 48
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
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
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
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
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
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
Yves L. Janin, “Preparation and Chemistry of 3/5-Halogenopyrazoles”, Chem. Rev., 112:7 (2012), 3924
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
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
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
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
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
L. Yet, Comprehensive Heterocyclic Chemistry III, 2008, 1
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
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