Skip to main content
SpringerLink
Log in

Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile and its reaction with substituted nitrile N-oxides

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

Abstract

A procedure of synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile has been developed and its reaction with substituted nitrile N-oxides has been investigated, proceeding by the mechanism of 1,3-dipolar cycloaddition and affording 2-methyl-5-[(1,2,4-oxadiazol-5-yl)(dinitro)methyl]-2H-tetrazoles. The latter react with KOH in ethanol forming the potassium salt of 2-methyltetrazol-5-yldinitromethane and substituted 5-hydroxy-1,2,4-oxadiazoles.

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. Ladyzhnikova, T.D., Altukhov, K.V., and Solov’ev, N.A., Zh. Org. Khim., 1986, vol. 22, p. 2618.

    CAS  Google Scholar 

  2. Tyrkov, A.G. and Resnyanskii, V.V., Izv. Vuzov, Ser. Khim. Khim. Tekhnol., 1994, vol. 37, p. 131.

    CAS  Google Scholar 

  3. Tyrkov, A.G. and Suikhanova, B.G., Zh. Org. Khim., 1999, vol. 35, p. 1330.

    Google Scholar 

  4. Terpigorev, A.N., Tselinskii, I.V., Makarevich, A.V., Frolova, G.M., and Mel’nikov, A.A., Zh. Org. Khim., 1987, vol. 23, p. 244.

    CAS  Google Scholar 

  5. Altukhov, K.V. and Perekalin, V.V., Russ. Chem. Rev., 1976, vol. 45, p. 2052; Shevelev, S.A., Dalinger, I.L., Vinogradov, V.M., and Fainzil’berg, A.F., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, p. 1816; Zeng, Z., Gao, H., Twamley, B., and Shreeve, J.M., J. Mater. Chem., 2007, vol. 17, p. 3819.

    Article  Google Scholar 

  6. Hantzsch, A. and Rickenberger, A., Ber., 1899, vol. 32, p. 628; Shevtsova, I.A. and Tyrkov, A.G., Russ. J. Org. Khim., 2007, vol. 43, p. 1742.

    Article  CAS  Google Scholar 

  7. Parker, C.O., Emmons, W.D., Rolewicz, H.A., and McCallum, K.S., Tetrahedron, 1962, vol. 17, p. 79; Parker, S.O. Tetrahedron, 1962, vol. 17, p. 109.

    Article  CAS  Google Scholar 

  8. Slovetskii, V.I., Shlyapochnikov, V.A., Shevelev, S.A., Fainzil’berg, A.A., and Novikov, S.S., Izv. Akad. Nauk SSSR, 1961, p. 330; Shlyapochnikov, V.A., Kolebatel’nye spektry alifaticheskikh nitrosoedinenii (Vibrational Spectra of Alifatic Nitrocompounds), Ivshin, V.P., Ed., Ioshkar-Ola: Izd. Udm. Gos. Iniv., 2007.

    Google Scholar 

  9. Ladyzhnikova, T.D., Solov’ev, N.A., Altukhov, K.V., and Perekalin, V.V., Zh. Org. Khim., 1988, vol. 24, p. 644.

    CAS  Google Scholar 

  10. Tyrkov, A.G., Doctoral Sci. (Chem.) Dissertation, Saratov, 2005.

    Google Scholar 

  11. Rubtsov, M.V. and Baichikov, A.G., Sinteticheskie khimiko-farmatsevticheskie preparaty (Synthetic Chemical Pharmaceitucal Medicines), Moscow: Meditsina, 1971.

    Google Scholar 

  12. Rheinboldt, H., Lieb. Ann., 1927, vol. 451, p. 161.

    Article  Google Scholar 

  13. Harada, K., Kaji, E., and Zen, S., Chem. Pharm. Bull., 1980, vol. 28, p. 3296.

    Article  CAS  Google Scholar 

  14. Adams, P., Kaiser, D.W., and Peters, G.A., J. Org. Chem., 1953, vol. 18, p. 934.

    Article  CAS  Google Scholar 

  15. Eloy, F., Fortsch. Chem. Forsch., 1965, vol. 4, p. 807.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Astrakhan State Universty, Astrakhan, Russia, 414000, Russia

    M. A. Abdelrakhim & A. G. Tyrkov

  2. Research Institute of Lepra Studies, Ministry of Public Health of the Russian Federation, Astrakhan, Russia

    E. A. Yurtaeva

Authors
  1. M. A. Abdelrakhim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. G. Tyrkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Yurtaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. G. Tyrkov.

Additional information

Original English Text © M.A. Abdelrakhim, A.G. Tyrkov, E.A. Yurtaeva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 287–291.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abdelrakhim, M.A., Tyrkov, A.G. & Yurtaeva, E.A. Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile and its reaction with substituted nitrile N-oxides. Russ J Org Chem 50, 280–284 (2014). https://doi.org/10.1134/S1070428014020237

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014020237

Keywords

Search

Navigation