SpringerLink
Log in

New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

New methods were developed for the synthesis of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide from 4-(tert-butyl-NNO-azoxy)-N-nitro-1,2,5-oxadiazol-3-amine or its alkali metal salts and acid anhydrides (or chlorides) in the presence of strong acids. The yield of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide in acetic anhydride in the presence of sulfuric acid or sulfuric anhydride at 20°C in 20 min attained 83%. A general mechanism was proposed for the reactions under study. Acetyl group behaved for the first time as departing group in the synthesis 1,2,3,4-tetrazine 1,3-dioxides, and [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide was obtained in 47% yield from N-[4-(acetyl-NNO-azoxy)-1,2,5-oxadiazol-3-yl]acetamide.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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. Churakov, A.M. and Tartakovsky, V.A., Chem. Rev., 2004, vol. 104, p. 2601.

    Article  CAS  Google Scholar 

  2. Pepekin, V.I., Matyushin, Yu.N., and Gubina, T.V., Russ. J. Phys. Chem. B, 2011, vol. 5, p. 97.

    Article  CAS  Google Scholar 

  3. Kiselev, V.G., Gritsan, N.P., Zarko, V.E., Kalmykov, P.I., and Shandakov, V.A., Combust. Explos., Shock Waves, 2007, vol. 43, p. 562.

    Article  Google Scholar 

  4. Zarko, V.E., Simonenko, V.N., Kalmykov, P.I., Kvasov, A.A., Chesnokov, E.N., and Kuper, K.E., Combust. Explos., Shock Waves, 2009, vol. 45, p. 752.

    Article  Google Scholar 

  5. Zarko, V.E., Kvasov, A.A., Ancharov, A.I., Kuper, K.E., Kiskin, A.B., and Simonenko, V.N., Proc. 40th Int. Conf. ICT, Karlsruhe, Germany, 2009, p. 98.

    Google Scholar 

  6. Kalmykov, P.I., Zarko, V.E., Sidel’nikov, A.A., Koptyug, I.V., Ancharov, A.I., and Sidorov, K.A., Russ. J. Appl. Chem., 2011, vol. 84, p. 248.

    Article  CAS  Google Scholar 

  7. Frumkin, A.E., Churakov, A.M., Strelenko, Yu.A., and Tartakovskii, V.A., Russ. Chem. Bull., 2000, vol. 49, p. 482.

    Article  CAS  Google Scholar 

  8. Churakov, A.M., Ioffe, S.L., and Tartakovsky, V.A., Mendeleev Commun., 1995, p. 227.

    Google Scholar 

  9. Churakov, A.M., Ioffe, S.L., and Tartakovsky, V.A., Mendeleev Commun., 1991, p. 101.

    Google Scholar 

  10. Churakov, A.M., Semenov, S.E., Ioffe, S.L., Strelenko, Yu.A., and Tartakovsky, V.A., Mendeleev Commun., 1995, p. 102.

    Google Scholar 

  11. Zelenov, V.P., Lobanova, A.A., and Sysolyatin, S.V., Materialy dokladov Mezhdunarodnoi nauchno-tekhnicheskoi i metodicheskoi konferentsii “Sovremennye problemy tekhnicheskoi khimii” (Proc. Int. Scientific-Technical and Methodical Conf. “Current Problems of Technical Chemistry”), Kazan’, 2004, p. 337.

    Google Scholar 

  12. Vinnik, M.I., Russ. Chem. Rev., 1966, vol. 35, p. 802.

    Article  Google Scholar 

  13. Spitzer, U.A., Toone, T.W., and Stewart, R., Can. J. Chem., 1976, vol. 54, p. 440.

    Article  CAS  Google Scholar 

  14. Houben, J., Die Methoden der organischen Chemie, Leipzig: Georg Thieme, 1939, vol. 4. Translated under the title Metody organicheskoi khimii, Moscow: Gos. Nauch.-Tekh. Izd. Khim. Lit., 1949, vol. 4, part 1, p. 292.

    Google Scholar 

  15. Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley, 1968, vol. 1. Translated under the title Reagenty dlya organicheskogo sinteza, Moscow: Mir, 1970, vol. 1, p. 82.

    Google Scholar 

  16. Tselinskii, I.V., Mel’nikova, S.F., and Vergizov, S.N., Chem. Heterocycl. Compd., 1981, vol. 17, p. 228.

    Article  Google Scholar 

  17. Kuznetsov, L.L. and Gidaspov, B.V., Zh. Org. Khim., 1975, no. 11, p. 2085.

    Google Scholar 

  18. Zelenov, V.P., Sysolyatin, S.V., and Lobanova, A.A., Abstracts of Papers, XVII Mendeleevskii s”ezd po obshchei i prikladnoi khimii (XVIIth Mendeleev Congr. on General and Applied Chemistry), Kazan’, 2003, vol. 1, p. 340.

    Google Scholar 

  19. Wandel’, A.P., Zelenov, V.P., Pankratova, G.A., Polyakov, S.V., and Sysolyatin, S.V., Russian Patent no. 2 122 972, 1998; Byull. Izobret., 1998, no. 34.

  20. Nekrasov, B.V., Osnovy obshchei khimii (Basic Principles of General Chemistry), Moscow: Khimiya, 1973, vol. 1, p. 431.

    Google Scholar 

  21. Remy, H., Lehrbuch der anorganischen Chemie, Leipzig: Geest and Portig, 1961, vol. 1. Translated under the title Kurs neorganicheskoi khimii, Moscow: Mir, 1966, vol. 1, p. 600.

    Google Scholar 

  22. Nelson, V., Serianz, A., and Kovacic, P., J. Org. Chem., 1976, vol. 41, p. 1751; Zawalski, R.C. and Kovacic, P., J. Org. Chem., 1979, vol. 44, p. 2130.

    Article  CAS  Google Scholar 

  23. Klenov, M.S., Zelenov, V.P., Churakov, A.M., Strelenko, Yu.A., and Tartakovskii, V.A., Russ. Chem. Bull., 2011, vol. 60, p. 2040.

    Article  CAS  Google Scholar 

  24. Gottardi, W., Monatsh. Chem., 1973, vol. 104, p. 421.

    Article  CAS  Google Scholar 

  25. Mel’nikova, T.M., Novikova, T.S., Khmel’nitskii, L.I., and Sheremetev, A.B., Mendeleev Commun., 2001, p. 30.

    Google Scholar 

  26. Zelenov, V.P. and Lobanova, A.A., Russ. Chem. Bull., 2011, vol. 60, p. 334.

    Article  CAS  Google Scholar 

  27. Zlotin, S.G., Vinogradova, E.A., and Luk’yanov, O.A., Mendeleev Commun., 1997, p. 7.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    V. P. Zelenov

  2. Altay Federal Research and Production Center, Biysk, Altay krai, Russia

    A. A. Lobanova & N. V. Sevodina

  3. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch, Russian Academy of Sciences, Biysk, Altay krai, Russia

    S. V. Sysolyatin

Authors
  1. V. P. Zelenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Lobanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Sysolyatin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Sevodina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Zelenov.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

Original Russian Text © V.P. Zelenov, A.A. Lobanova, S.V. Sysolyatin, N.V. Sevodina, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 3, pp. 467–477.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zelenov, V.P., Lobanova, A.A., Sysolyatin, S.V. et al. New syntheses of [1,2,5]oxadiazolo[3,4-e][1,2,3,4]tetrazine 4,6-dioxide. Russ J Org Chem 49, 455–465 (2013). https://doi.org/10.1134/S107042801303024X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801303024X

Keywords

Search

Navigation