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Synthesis and investigation of isomeric mono- and dinitro derivatives of 3-methyl-4-(pyrazol-3-yl)furazan

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Chemistry of Heterocyclic Compounds Aims and scope

The regioselective introduction of nitro groups in pyrazoles, containing a furazanyl substituent at position 3(5) was investigated. All synthetically accessible isomeric mono- and dinitropyrazole derivatives were obtained. X-ray structural investigation was performed for all mononitroisomers and a dinitro derivative.

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References

  1. Fustero, S.; Simón-Fuentes, A.; Sanz-Cervera, J. F. Org. Prep. Proced. Int. 2009, 41, 253.

    Article  CAS  Google Scholar 

  2. Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 1423.

    Article  CAS  Google Scholar 

  3. Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 2897.

    Article  CAS  Google Scholar 

  4. Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111, 6984.

    Article  CAS  Google Scholar 

  5. Janin, Y. L. Chem. Rev. 2012, 112, 3924.

    Article  CAS  Google Scholar 

  6. Pizzuti, L.; Barschak, A. G.; Stefanello, F M.; Farias, M. D.; Lencina, C.; Roesch-Ely, M.; Cunico, W.; Moura, S.; Pereira, C. M. P. Curr. Org. Chem. 2014, 18, 115.

    Article  CAS  Google Scholar 

  7. Pérez-Fernández, R.; Goya, P.; Elguero, J. ARKIVOC 2014, (ii), 233.

  8. Chauhan, S.; Paliwal, S.; Chauhan, R. Synth. Commun. 2014, 44, 1333.

    Article  CAS  Google Scholar 

  9. Kumari, S.; Paliwal, S.; Chauhan, R. Synth. Commun. 2014, 44, 1521.

    Article  CAS  Google Scholar 

  10. Hervé, G.; Roussel, C.; Graindorge, H. Angew. Chem., Int. Ed. 2010, 49, 3177.

    Article  Google Scholar 

  11. Dalinger, I.; Shevelev, S.; Korolev, V.; Khakimov, D.; Pivina, T.; Pivkina, A.; Ordzhonikidze, O.; Frolov, Y. J. Therm. Anal. Calorim. 2011, 105, 509.

    Article  CAS  Google Scholar 

  12. Nelyubina, Y. V.; Dalinger, I. L.; Lyssenko, K. A. Angew. Chem., Int. Ed. 2011, 50, 2892.

    Article  CAS  Google Scholar 

  13. Zhang, Y.; Parrish, D.A.; Shreeve, J. M. Chem.–Eur. J. 2012, 18, 987.

    Article  CAS  Google Scholar 

  14. Wang, Y.-L.; Zhao, F.-Q.; Ji, Y.-P.; Pan, Q.; Yi, J.-H.; An, T.; Wang, W.; Yu, T.; Lu, X.-M. J. Anal. Appl. Pyrolysis 2012, 98, 231.

    Article  CAS  Google Scholar 

  15. Zhang, J.; He, C.; Parrish, D. A.; Shreeve, J. M. Chem.–Eur. J. 2013, 19, 8929.

    Article  CAS  Google Scholar 

  16. Zhang, W.; Huang, J.; Xu, K.; An, T.; Yang, S.; Song, J.; Zhao, F. J. Anal. Appl. Pyrolysis 2013, 104, 703.

    Article  CAS  Google Scholar 

  17. He, C.; Zhang, J.; Parrish, D. A.; Shreeve, J. M. J. Mater. Chem. A 2013, 1, 2863.

    Article  CAS  Google Scholar 

  18. Yin, P.; Zhang, J.; Parrish, D. A.; Shreeve, J. M. Chem. Eur. J. 2014, 20, 16529.

    Article  CAS  Google Scholar 

  19. Yin, P.; Zhang, J.; He, C.; Parrish, D. A.; Shreeve, J. M. J. Mater. Chem. A 2014, 2, 3200.

    Article  CAS  Google Scholar 

  20. Li, C.; Liang, L.; Wang, K.; Bian, C.; Zhang, J.; Zhou, Z. J. Mater. Chem. A 2014, 2, 18097.

    Article  CAS  Google Scholar 

  21. Boyer, J. H. Nitroazoles: The C-Nitro Derivatives of Five-Membered N- and N,O-Heterocycles (Organic Nitro Chemistry Series); VCH: Weinheim, 1986.

    Google Scholar 

  22. Kanischev, M. I.; Korneeva, N. V.; Shevelev, S. A.; Fainzilberg, A. A. Chem. Heterocycl. Compd. 1988, 24, 353. [Khim. Geterotsikl. Soedin. 1988, 435.]

  23. Shevelev, S. A.; Dalinger, I. L. Russ. J. Org. Chem. 1998, 34, 1071. [Zh. Org. Khim. 1998, 34, 1127.]

  24. Zaitsev A. A.; Dalinger, I. L.; Shevelev, S. A. Russ. Chem. Rev. 2009, 78, 589. [Usp. Khim. 2009, 78, 643.]

  25. Larina, L.; Lopyrev, V. Nitroazoles. Synthesis, Structure and Applications; Springer LLC: New York, 2009.

    Book  Google Scholar 

  26. Dalinger, I. L.; Shkinyova, T. K.; Shevelev, S. A.; Kuz'min, V. S.; Arnautova, E. A.; Pivina, T. S. In Energetic Materials. Production, Processing and Characterization, 29th International Annual Conference of ICT, Karlsruhe, June 30 – July 3, 1998; Fraunhofer ICT: Pfinztal, 1998, p. 57.

  27. Dalinger, I. L.; Shkineva, T. K.; Vatsadze, I. A.; Popova, G. P.; Shevelev, S. A. Mendeleev Commun. 2011, 21, 48.

    Article  CAS  Google Scholar 

  28. Dalinger, I. L.; Vinogradov, V. M.; Shevelev, S. A.; Kuz'min, V. S. Mendeleev Commun. 1996, 6, 13.

    Article  Google Scholar 

  29. Dalinger, I. L.; Vinogradov, V. M.; Shevelev, S. A.; Kuz'min, V. S.; Arnautova, E. A.; Pivina, T. S. Propellants, Explos., Pyrotech. 1998, 23, 212.

    Article  CAS  Google Scholar 

  30. Semenov V. V.; Ugrak, B. I.; Shevelev, S. A.; Kanischev, M. I.; Baryshnikov, A. T.; Fainzilberg, A. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39, 1658. [Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 1827.]

  31. Ananikov, V. P., Khokhlova, E. A. Egorov, M. P.; Sakharov, A. M.; Zlotin, S. G.; Kucherov, A. V.; Kustov, L. M.; Gening, M. L.; Nifantiev, N. E. Mendeleev Commun. 2015, 25, 75.

    Article  CAS  Google Scholar 

  32. Stepanov, A. I.; Dashko, D. V.; Astrat'ev, A. A. Cent. Eur. J. Energ. Mater. 2012, 9, 329.

    CAS  Google Scholar 

  33. Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu. Mendeleev Commun. 2012, 22, 302.

    Article  CAS  Google Scholar 

  34. Stepanov, A. I.; Astrat'ev, A. A.; Dashko, D. V.; Spiridonova N. P.; Mel'nikova, S. F.; Tselinskii, I. V. Russ. Chem. Bull. 2012, 61, 1024. [Izv. Akad. Nauk, Ser. Khim. 2012, 1019.]

  35. Dippold, A. A.; Klapötke, T. M. Chem. – Asian J. 2013, 8, 1463.

    Article  CAS  Google Scholar 

  36. Stepanov, A. I.; Dashko, D. V.; Astrat'ev, A. A. Chem. Heterocycl. Compd. 2013, 49, 776. [Khim. Geterotsikl. Soedin. 2013, 830.]

  37. Sheremetev, A. B.; Aleksandrova, N. S.; Palysaeva, N. V.; Struchkova, M. I.; Tartakovsky, V. A.; Suponitsky, K. Yu. Chem.–Eur. J. 2013, 19, 12446.

    Article  CAS  Google Scholar 

  38. Chand, D.; Parrish, D. A.; Shreeve, J. M. J. Mater. Chem. A 2013, 1, 15383.

    Article  CAS  Google Scholar 

  39. Parakhin, V. V.; Luk'yanov, O. A. Russ. Chem. Bull. 2013, 62, 2007. [Izv. Akad. Nauk, Ser. Khim. 2013, 2007.]

  40. Zhang, J.; Parrish, D. A.; Shreeve, J. M. Chem. – Asian J. 2014, 9, 2953.

    Article  CAS  Google Scholar 

  41. Palysaeva, N. V.; Kumpan, K. P.; Struchkova, M. I.; Dalinger, I. L.; Kormanov, A. V.; Aleksandrova, N. S.; Chernyshev, V. M.; Pyreu, D. F.; Suponitsky, K. Yu.; Sheremetev, A. B. Org. Lett. 2014, 16, 406.

    Article  CAS  Google Scholar 

  42. Kettner, M. A.; Klapötke, T. M. Chem. Commun. 2014, 2268.

  43. Voronin, A. A.; Zelenov, V. P.; Churakov, A. M.; Strelenko, Yu. A.; Tartakovsky, V. A. Russ. Chem. Bull. 2014, 63, 475. [Izv. Akad. Nauk, Ser. Khim. 2012, 475.]

  44. Wei, H.; Gao, H.; Shreeve, J. M. Chem.–Eur. J. 2014, 20, 16943.

    Article  CAS  Google Scholar 

  45. Kettner, M. A.; Klapötke, T. M. Chem.–Eur. J. 2015, 21, 3755.

    Article  CAS  Google Scholar 

  46. Klapötke, T. M.; Schmid, P. C.; Schnell, S.; Stierstorfer, J. J. Mater. Chem. A 2015, 3, 2658.

    Article  Google Scholar 

  47. Sheremetev, A. B.; Aleksandrova, N. S. in Current Problems of Special Technical Chemistry [in Russian], Materials of International Scientific-Technical and Methodological Conference, December 21–22, 2007, Kazan; Izd-vo Kazan State Technological University: Kazan, 2007, p. 107.

  48. Stepanov, A. I.; Sannikov, V. S.; Dashko, D. V.; Astrat'ev, А. А. Izv. SPbGTI(TU) 2014, (26), 42.

  49. Sheremetev, A. B.; Yudin, I. L.; Palysaeva, N. V.; Suponitsky, K. Yu. J. Heterocycl. Chem. 2012, 49, 394.

    Article  CAS  Google Scholar 

  50. Suponitsky, K. Yu.; Chernyshev, V. M.; Palysaeva, N. V.; Sheremetev, A. B. Acta Cryst., Sect. E: Struct. Rep. Online 2013, E69, o1648.

    Article  Google Scholar 

  51. Elassar, A.-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463.

    Article  CAS  Google Scholar 

  52. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433.

    Article  CAS  Google Scholar 

  53. Sheremetev, A. B. Russ. Chem. Rev. 1999, 68, 137. [Usp. Khim. 1999, 68, 154.]

  54. Sheremetev, A. B.; Makhova, N. N.; Friedrichsen, W. Adv. Heterocycl. Chem. 2001, 78, 65.

    Article  CAS  Google Scholar 

  55. Zelenov, M. P.; Frolova, G. M.; Melnikova, S. F.; Tselinskii, I. V. J. Org. Chem. 1982, 18. [Zh. Org. Khim. 1982, 18, 27.]

  56. Calvino, R.; Ferrarotti, B.; Gasco, A.; Serafino, A. J. Heterocycl. Chem. 1983, 20, 1419.

    Article  CAS  Google Scholar 

  57. Sheremetev, A. B.; Konkina, S. M.; Dmitriev, D. E. Russ. Chem. Bull. 2007, 56, 1575. [Izv. Akad. Nauk, Ser. Khim. 2007, 1516.]

  58. Shevelev, S. A.; Dalinger, I. L.; Shkineva, T. K.; Ugrak, B. I. Russ. Chem. Bull. 1993, 42, 1857. [Izv. Akad. Nauk, Ser. Khim. 1993, 1941.] Chemistry of Heterocyclic Compounds 2015, 51(6), 545–552

  59. Dmitriev, D. E.; Strelenko, Yu. A.; Sheremetev, A. B. Russ. Chem. Bull. 2002, 51, 290. [Izv. Akad. Nauk, Ser. Khim. 2002, 277.]

  60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Kudin, K. N., Jr.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01, Gaussian, Inc.: Wallingford, 2004.

    Google Scholar 

  61. Sheremetev, A. B.; Aleksandrova, N. S.; Suponitsky, K. Yu.; Antipin, M. Yu.; Tartakovsky, V. A. Mendeleev Commun. 2010, 20, 249.

    Article  CAS  Google Scholar 

  62. Suponitsky, K. Yu.; Masunov, A. E.; Antipin, M. Yu. Mendeleev. Commun. 2008, 18, 265.

    Article  CAS  Google Scholar 

  63. Suponitsky, K. Y.; Liao, Y.; Masunov, A. E. J. Phys. Chem. A 2009, 113, 10994.

    Article  CAS  Google Scholar 

  64. Suponitsky, K. Yu.; Masunov, A. E. J. Chem. Phys. 2013, 139, 094310.

    Article  Google Scholar 

  65. Suponitsky, K. Yu.; Lyssenko, K. A.; Ananyev, I. V.; Kozeev, A. M.; Sheremetev, A. B. Cryst. Growth Des. 2014, 14, 4439.

    Article  CAS  Google Scholar 

  66. Sheremetev, A. B.; Lyalin, B. V.; Kozeev, A. M.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu. RSC Adv. 2015, 5, 37617.

    Article  CAS  Google Scholar 

  67. Dalinger, I. L.; Vatsadze, I. A.; Shkineva, T. K.; Kormanov, A. V.; Struchkova, M. I.; Suponitsky, K. Yu.; Bragin, A. A.; Monogarov, K. A.; Sinditskii, V. P.; Sheremetev, A. B. Chem. – Asian J. 2015. DOI: 10.1002/asia.201500533.

    Google Scholar 

  68. Suponitsky, K. Yu.; Lyssenko K. A.; Antipin, M. Yu.; Aleksandrova, N. S.; Sheremetev, A. B.; Novikova T. S. Russ. Chem. Bull. 2009, 58, 2129. [Izv. Akad. Nauk, Ser. Khim. 2009, 2065].

  69. Averkiev, B. B.; Antipin, M. Yu.; Sheremetev, A. B.; Timofeeva, T. V. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2003, 59, o383.

    Article  Google Scholar 

  70. Sheremetev, A. B.; Yudin, I. L.; Suponitsky, K. Yu. Mendeleev Commun. 2006, 16, 264.

    Article  Google Scholar 

  71. Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu.; Antipin, M. Yu. Eur. J. Org. Chem., 2012, 2266.

  72. Sheremetev, A. B.; Kozeev, A. M.; Aleksandrova, N. S.; Struchkova, M. I.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2013, 49, 1358. [Khim. Geterotsikl. Soedin. 2013, 1457.]

  73. Sheremetev, A. B.; Zabusov, S. G; Tukhbatshin, T. R.; Palysaeva, N. V.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2014, 50, 1154. [Khim. Geterotsikl. Soedin. 2014, 1250.]

  74. Catalan, J.; Abboud, J. L. M.; Elguero, J. Adv. Heterocycl. Chem. 1987, 41, 187.

    Article  CAS  Google Scholar 

  75. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

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This work received financial support from the Russian Science Fund (RSF project 14-13-01153).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Igor L. Dalinger, Irina A. Vatsadze, Tatyana K. Shkineva, Alexandr V. Kormanov, Andrei M. Kozeev & Aleksei B. Sheremetev

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Boris B. Averkiev

  3. Stockton University, 101 Vera King Farris Drive, Galloway, New Jersey, 08205, USA

    Boris B. Averkiev

  4. M. V. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 11999, Russia

    Alexandr I. Dalinger & Mikhail K. Beklemishev

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  1. Igor L. Dalinger
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  2. Irina A. Vatsadze
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  3. Tatyana K. Shkineva
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Correspondence to Aleksei B. Sheremetev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 545–552

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Dalinger, I.L., Vatsadze, I.A., Shkineva, T.K. et al. Synthesis and investigation of isomeric mono- and dinitro derivatives of 3-methyl-4-(pyrazol-3-yl)furazan. Chem Heterocycl Comp 51, 545–552 (2015). https://doi.org/10.1007/s10593-015-1739-9

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