Skip to main content
SpringerLink
Log in

3-(1-Methyl-1-nitroethyl-1-ONN-azoxy)-4-aminofuroxan. Synthesis and transformations of the amino group

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A four-step procedure to convert 4-(1-methyl-1-nitroethyl-1-ONN-azoxy)-3-cyanofuroxan into 3-(1-methyl-1-nitroethyl-1-ONN-azoxy)-4-aminofuroxan was developed. The pathways of transformation of the amino group of the synthesized compound into N-nitramino-, N-alkyl-N-nitramino-, N,N’-methylenediamino-, N,N’-methylene-N,N’-dinitramino-, and azo groups were studied.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. V. Parakhin, O. A. Luk’yanov, Russ. Chem. Bull., 2016, 65: 295.

    Article  CAS  Google Scholar 

  2. V. V. Parakhin, N. I. Shlykova, O. A. Luk’yanov, Russ. Chem. Bull., 2017, 66: 320.

    Article  CAS  Google Scholar 

  3. F. R. Sullivan, E. Luck, P. Kovacic, J. Org. Chem., 1974, 39: 2967.

    Article  CAS  Google Scholar 

  4. V. Nelson, A. Serianz, P. Kovacic, J. Org. Chem., 1976, 41: 1751.

    Article  CAS  Google Scholar 

  5. S. G. Zlotin, O. A. Luk’yanov, Russ. Chem. Rev., 1993, 62: 143.

    Article  Google Scholar 

  6. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I. Shlykova, Yu. B. Salamonov, Russ. Chem. Bull., 2009, 58: 2063.

    Article  CAS  Google Scholar 

  7. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I. Shlykova, M. E. Shagaeva, Russ. Chem. Bull., 2011, 60: 1703.

    Article  CAS  Google Scholar 

  8. O. A. Luk’yanov, V. V. Parakhin, G. V. Pokhvisneva, T. V. Ternikova, Russ. Chem. Bull., 2012, 61: 355.

    Article  CAS  Google Scholar 

  9. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I. Shlykova, Russ. Chem. Bull., 2012, 61: 360.

    Article  CAS  Google Scholar 

  10. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, Russ. Chem. Bull., 2012, 61: 1783.

    Article  CAS  Google Scholar 

  11. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, Russ. Chem. Bull., 2015, 64: 137.

    Article  CAS  Google Scholar 

  12. E. N. Zil’berman, Reaktsii nitrilov [Reactions of nitriles], Khimiya, Moscow, 1972, p. 103 (in Russian).

  13. A. Gasco, V. Mortarini, G. Rua, E. Menziani, J. Heterocycl. Chem., 1972, 9: 837.

    Article  CAS  Google Scholar 

  14. A. S. Kulikov, I. V. Ovchinnikov, S. I. Molotov, N. N. Makhova, Russ. Chem. Bull., 2003, 52: 1822.

    Article  CAS  Google Scholar 

  15. A. O. Finogenov, A. S. Kulikov, M. A. Epishina, I. V. Ovchinnikov, Yu. V. Nelyubina, N. N. Makhova, J. Heterocycl. Chem., 2013, 50: 135.

    Article  CAS  Google Scholar 

  16. I. V. Ovchinnikov, A. N. Blinnikov, N. N. Makhova, L. I. Khmel’nitskii, Mendeleev Commun., 1995, 5: 58.

    Article  Google Scholar 

  17. E. L. Baryshnikova, A. S. Kulikov, I. V. Ovchinnikov, V. V. Solomentsev, N. N. Makhova, Mendeleev Commun., 2001, 11: 230.

    Article  CAS  Google Scholar 

  18. A. R. Gagneux, R. Meier, Helv. Chim. Acta, 1970, 53: 1883.

    Article  CAS  Google Scholar 

  19. L. I. Khmel’nitskii, S. S. Novikov, T. I. Godovikova, Khimiya furoksanov: reaktsii i primenenie [Chemistry of Furoxans. Reactions and Applications], 2nd ed., Nauka, Moscow, 1996, p. 13 (in Russian).

    Google Scholar 

  20. V. P. Zelenov, A. A. Voronin, A. M. Churakov, M. S. Klenov, Yu. A. Strelenko, V. A. Tartakovsky, Russ. Chem. Bull., 2011, 60: 2046.

    Article  CAS  Google Scholar 

  21. Ch. He, Yo. Tang, L. A. Mitchell, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2016, 4: 8969.

    Article  CAS  Google Scholar 

  22. L. I. Khmel’nitskii, S. S. Novikov, T. I. Godovikova, Khimiya furoksanov: reaktsii i primenenie [Chemistry of Furoxans. Reactions and Applications], 2nd ed., Nauka, Moscow, 1996, p. 53 (in Russian).

    Google Scholar 

  23. A. Yu. Tyurin, A. M. Churakov, Yu. A. Strelenko, M. O. Ratnikov, V. A. Tartakovsky, Russ. Chem. Bull., 2006, 55: 1648.

    Article  CAS  Google Scholar 

  24. M. S. Klenov, M. O. Ratnikov, A. M. Churakov, V. N. Solkan, Yu. A. Strelenko, V. A. Tartakovsky, Russ. Chem. Bull., 2011, 60: 536.

    Article  CAS  Google Scholar 

  25. O. A. Luk’yanov, V. V. Parakhin, Russ. Chem. Bull., 2012, 61: 1582.

    Article  CAS  Google Scholar 

  26. A. O. Finogenov, M. A. Epishina, A. S. Kulikov, N. N. Makhova, I. V. Anan’ev, V. A. Tartakovsky, Russ. Chem. Bull., 2010, 59: 2108.

    Article  CAS  Google Scholar 

  27. N. N. Makhova, I. V. Ovchinnikov, B. N. Khasanov, L. I. Khmel’nitskii, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982, 31: 573.

    Article  Google Scholar 

  28. A. N. Blinnikov, N. N. Makhova, L. I. Khmel’nitskii, Mendeleev Commun., 1999, 9: 15.

    Article  Google Scholar 

  29. I. V. Ovchinnikov, A. S. Kulikov, N. N. Makhova, P. Tosco, A. Di Stilo, R. Fruttero, A. Gasco, Farmaco, 2003, 58: 677.

    Article  CAS  PubMed  Google Scholar 

  30. L. Liang, K. Wang, Ch. Bian, L. Ling, Zh. Zhou, Chem. Eur. J., 2013, 19: 14902.

    Article  CAS  PubMed  Google Scholar 

  31. I. V. Ovchinnikov, N. N. Makhova, L. I. Khmel’nitskii, V. S. Kuz’min, L. N. Akimova, V. I. Pipekin, Dokl. Chem., 1998, 359: 67.

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    V. V. Parakhin, P. B. Gordeev & O. A. Luk’yanov

Authors
  1. V. V. Parakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. B. Gordeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. A. Luk’yanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Parakhin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1065–1071, June, 2018.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Parakhin, V.V., Gordeev, P.B. & Luk’yanov, O.A. 3-(1-Methyl-1-nitroethyl-1-ONN-azoxy)-4-aminofuroxan. Synthesis and transformations of the amino group. Russ Chem Bull 67, 1065–1071 (2018). https://doi.org/10.1007/s11172-018-2181-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-018-2181-9

Key words

Search

Navigation