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Synthesis and structural investigation of 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide

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Abstract

The oxidation of hexane-2,3,4,5-tetraone tetraoxime with dinitrogen tetroxide was studied in different solvents. The primary furoxan ring closure was found to occur involving either two central or two terminal oxime groups to form 4,7-dimethyl[1,2,5]oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide and the previously unknown 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide. The structure of the latter compound was established by X-ray diffraction.

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References

  1. A. Horton, K. Nash, E. Tackie-Yarboi, A. Kostrevski, A. Novak, A. Raghavan, J. Tulsulkar, Q. Alhadidi, N. Wamer, B. Langenderfer, K. Royster, M. Ducharme, K. Hagood, M. Post, Z. A. Shah, I. T. Schiefer, J. Med. Chem., 2018, 61, 4593.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. S. Atlante, K. Chegaev, C. Cencioni, S. Guglielmo, E. Marini, E. Borretto, C. Gaetano, R. Fruttero, F. Spallotta, L. Lazzarato, Eur. J. Med. Chem., 2018, 144, 612.

    Article  CAS  PubMed  Google Scholar 

  3. N. E. Ustyuzhanina, L. L. Fershtat, M. L. Gening, N. E. Nifantiev, N. N. Makhova, Mendeleev Commun., 2018, 28, 49.

    Article  CAS  Google Scholar 

  4. A. S. Kulikov, A. A. Larin, L. L. Fershtat, L. V. Anikina, S. A. Pukhov, S. G. Klochkov, M. I. Struchkova, A. A. Romanova, I. V. Ananyev, N. N. Makhova, Arkivoc, 2017, 250.

    Google Scholar 

  5. N. E. Ustyuzhanina, L. L. Fershtat, M. L. Gening, N. E. Nifantiev, N. N. Makhova, Mendeleev Commun., 2016, 26, 513.

    Article  CAS  Google Scholar 

  6. L. S. Konstantinova, S. A. Amelichev, S. G. Zlotin, M. I. Struchkova, T. I. Godovikova, O. A. Rakitin, Mendeleev Commun., 2015, 25, 339.

    Article  CAS  Google Scholar 

  7. L. L. Fershtat, M. A. Epishina, A. S. Kulikov, N. N. Makhova, Mendeleev Commun., 2015, 25, 36.

    Article  CAS  Google Scholar 

  8. L. L. Fershtat, M. A. Epishina, A. S. Kulikov, I. V. Ovchinnikov, I. V. Ananyev, N. N. Makhova, Tetrahedron, 2015, 71, 6764.

    Article  CAS  Google Scholar 

  9. L. L. Fershtat, A. A. Larin, M. A. Epishina, I. V. Ovchinnikov, A. S. Kulikov, I. A. Ananyev, N. N. Makhova, RSC Advances, 2016, 6, 31526.

    Article  CAS  Google Scholar 

  10. L. L. Fershtat, S. S. Ashirbaev, V. V. Kachala, N. N. Ma khova, Mendeleev Commun., 2015, 25, 257.

    Article  CAS  Google Scholar 

  11. N. V. Orlov, Russ. Chem. Bull., 2016, 65, 1418.

    Article  CAS  Google Scholar 

  12. A. M. Starosotnikov, M. A. Bastrakov, A. A. Pavlov, I. V. Fedyanin, I. L. Dalinger, S. A. Shevelev, Mendeleev Commun., 2016, 26, 217..

    Article  CAS  Google Scholar 

  13. V. G. Granik, N. B. Grigor’ev, Russ. Chem. Rev., 2011, 80, 171.

    Article  CAS  Google Scholar 

  14. A. Gasco, K. Schoenafinger, The NO-Releasing Heterocycles, in Nitric Oxide Donors, Eds P. G. Wang, T. B. Cai, N. Taniguchi, WILEY-VCH Verlag GmbH & Co KGaA, Wein heim, 2005, p. 131.

    Google Scholar 

  15. T. Wang, A. J. van der Vlies, H. Uyama, U. Hasegawa, Polym. Chem., 2015, 6, 7737.

    Article  CAS  Google Scholar 

  16. W. H. Poh, N. Barraud, S. Guglielmo, L. Lazzarato, B. Rolando, R. Fruttero, S. A. Rice, ACS Chem. Biol., 2017, 12, 2097.

    Article  CAS  PubMed  Google Scholar 

  17. A. Gasco, R. Fruttero, G. Sorba, A. Di Stilo, R. Calvino, Pure Appl. Chem., 2004, 76, 973.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. S. G. Zlotin, A. M. Churakov, I. L. Dalinger, O. A. Luk’yanov, N. N. Makhova, A. Yu. Sukhorukov, V. A. Tartakovsky, Mendeleev Commun., 2017, 27, 535.

    Article  CAS  Google Scholar 

  20. L. L. Fershtat, N. N. Makhova, Russ. Chem. Rev., 2016, 85, 1097.

    Article  CAS  Google Scholar 

  21. D. Fischer, T. M. Klapötke, J. Stierstorfer, Eur. J. Inorg. Chem., 2014, 5808.

    Google Scholar 

  22. L. L. Fershtat, A. A. Larin, M. A. Epishina, A. S. Kulikov, I. V. Ovchinnikov, I. V. Ananyev, N. N. Makhova, Tetrahedron Lett., 2016, 57, 4268.

    Article  CAS  Google Scholar 

  23. B. L. Marquez, W. H. Gerwick, R. T. Williamson, Magn. Reson. Chem., 2001, 39, 499.

    Article  CAS  Google Scholar 

  24. R. T. Williamson, B. L. Marquez, W. H. Gerwick, K. E. Kover, Magn. Reson. Chem., 2000, 38, 265.

    Article  CAS  Google Scholar 

  25. Yu. A. Strelenko, O. A. Rakitin, T. I. Godovikova, L. I. Khmel’nitskii, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 2649].

    Article  Google Scholar 

  26. V. A. Ogurtsov, A. V. Shastin, S. G. Zlotin, O. A. Rakitin, Tetrahedron Lett., 2016, 57, 4027.

    Article  CAS  Google Scholar 

  27. G. Ponzio, V. Bernardi, Gazz. Chim. Ital., 1925, 55, 67.

    CAS  Google Scholar 

  28. R. Calvino, R. Fruttero, D. Ghigo, A. Bosia, G. P. Pescarmona, A. Gasco, J. Med. Chem., 1992, 35, 3296.

    Article  CAS  PubMed  Google Scholar 

  29. G. Dannhardt, I. Obergrusberger, Archiv Pharm., 1989, 322, 513.

    Article  CAS  Google Scholar 

  30. O. Das, S. Paria, T. K. Paine, Tetrahedron Lett., 2008, 49, 5924.

    Article  CAS  Google Scholar 

  31. G. Ponzio, Gazz. Chim. Ital., 1936, 66, 479.

    CAS  Google Scholar 

  32. T. G. G. Battye, L. Kontogiannis, O. Johnson, H. R. Powell, A. G. W. Leslie, Acta Cryst., 2011, D67, 271.

    Google Scholar 

  33. P. Evans, Acta Cryst., 2006, D62, 72.

    Google Scholar 

  34. G. M. Sheldrick, Acta Cryst., 2015, C71, 3.

    Google Scholar 

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Authors and Affiliations

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

    N. V. Obruchnikova, R. A. Novikov, S. G. Zlotin & O. A. Rakitin

  2. National Research Center “Kurchatov Institute”, 1 ul. Akad. Kurchatova, 123182, Moscow, Russian Federation

    P. V. Dorovatovskii & V. N. Khrustalev

  3. Peoples’ Friendship University of Russia (RUDN University), 6 ul. Miklukho-Maklaya, 117198, Moscow, Russian Federation

    V. N. Khrustalev

Authors
  1. N. V. Obruchnikova
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  2. R. A. Novikov
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  3. S. G. Zlotin
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  4. P. V. Dorovatovskii
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  5. V. N. Khrustalev
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  6. O. A. Rakitin
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Corresponding author

Correspondence to O. A. Rakitin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2044–2048, November, 2018.

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Obruchnikova, N.V., Novikov, R.A., Zlotin, S.G. et al. Synthesis and structural investigation of 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide. Russ Chem Bull 67, 2044–2048 (2018). https://doi.org/10.1007/s11172-018-2326-x

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  • DOI: https://doi.org/10.1007/s11172-018-2326-x

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