Skip to main content
SpringerLink
Log in

Alkenyl derivatives of 5-nitro-2-pyridone: Synthesis and halocyclization

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

Abstract

Alkylation of 5-nitro-2-pyridone by alkenyl halides in acetone in the presence of K2СО3 proceeds with generation of a mixture of N- and О-derivatives with N-isomer prevailing. 1-Allyl- and 1-methylallyl-5-nitro-2-pyridone react with halogens with the formation of 2-halomethyl-6-nitro-2,3-dihydrooxazolo[3,2-a]-pyridinium halides. 1-Prenyl-5-nitro-2-pyridone reacts with bromine with the formation of 3-bromine-2,2-dimethyl-7-nitro-3,4-dihydro-2Н-pyrido[2,1-b][1,3]oxazinium bromide, and with iodine giving 2,2-dimethyl-7-nitro-3,4-dihydro-2Н-pyrido[2,1-b][1,3]oxazinium triiodide.

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. Fujimato, K., Morisaki, D., Yoshida, M., Namba, T., Hye-Sook, K., Wataya, Y., Kourai, H., Kakuta, H., and Sasaki, K., Bioorg. Med. Chem., 2006, vol. 16, p. 2758.

    Article  Google Scholar 

  2. Ilies, M.A., Seitz, W.A., Johnson, B.H., Ezell, E.L., Miller, A.L., Thompson, E.B., and Balaban, A.T., J. Med. Chem., 2006, vol. 49, p. 3872.

    Article  CAS  Google Scholar 

  3. Riahi, A., Wurster, M., Lalk, M., Lindequist, U., and Langer, P., Bioorg. Med. Chem., 2009, vol. 17, p. 4323.

    Article  CAS  Google Scholar 

  4. Rusinov, V.L. and Chupakhin, O.N., Nitroaziny (Nitroazines), Novosibirsk Nauka, 1991.

    Google Scholar 

  5. Chung, N.M. and Tieckelmann, H., J. Org. Chem., 1970, vol. 35, p. 2517.

    Article  CAS  Google Scholar 

  6. Mikhant’ev, B.I., Fedorov, E.I., Kucherova, A.I., and Potapova, V.I., Zh. Obshch. Khim., 1959, vol. 29, p. 1874.

    Google Scholar 

  7. Vershinina, E.A. and Kim, D.G., Vestn. YuUrGU, Ser. Khim., 2010, vol. 31, p. 10.

    Google Scholar 

  8. Lebedev, A.T., Mass-spektrometriya v organicheskoi khimii, (Mass Spectrometry in Organic Chemistry), Moscow Binom, Laboratoriya znanii, 2003.

    Google Scholar 

  9. Kim, D.G. and Berdnikova, E.V., Vestn. YuUrGU, Ser. Khim., 2012, vol. 24, p. 13.

    Google Scholar 

  10. Vul’fson, N.S., Zaikin, V.G., and Mikaya, A.I., Massspektrometriya organicheskikh soedinenii (Mass Spectrometry of Organic Compounds), Moscow Khimiya, 1986.

    Google Scholar 

  11. Kim, D.G., Alalykina, N.P., and Sogrina, E.I., Zh. Org. Khim., 1985, vol. 21, p. 2022.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. South Ural State University (National Research University), pr. Lenina 76, Chelyabinsk, 454080, Russia

    E. V. Kalita & D. G. Kim

  2. Ural Federal University, Yekaterinburg, Russia

    O. S. Yeltsov & T. S. Shtukina

Authors
  1. E. V. Kalita
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. G. Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. S. Yeltsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. S. Shtukina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Kalita.

Additional information

Original Russian Text © E.V. Kalita, D.G. Kim, O.S. Yeltsov, T.S. Shtukina, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1157–1161.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kalita, E.V., Kim, D.G., Yeltsov, O.S. et al. Alkenyl derivatives of 5-nitro-2-pyridone: Synthesis and halocyclization. Russ J Org Chem 52, 1148–1153 (2016). https://doi.org/10.1134/S1070428016080091

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016080091

Search

Navigation