Skip to main content
SpringerLink
Log in

Sigma-complexes in the pyrimidine series. 11. 5-arylazo-5-nitro-2,5- and -4,5-dihydro-pyrimidines from anionic sigma complexes of 5-nitropyrimidine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have studied the reaction of acetonyl anionic sigma complexes of 5-nitropyrimidines with aryldiazonium salts. We have established that, independently of the position of the geminal unit in the sigma complex, electrophilic attack by the diazonium ion occurs at the C(5) atom with formation of 5-arylazo-5-nitro-2,5- and 4,5-dihydropyrimidines. The latter are unstable and upon isolation are converted to N-methoxycarbonyl-N′-(1-acetonyl-2-nitro-2-arylhydrazono)ethyl-O-methylisourea. The structure of one of these compounds has been proven by x-ray diffraction. Under alkaline conditions, aromatization of 2,5-dihydropyrimidines to 5-arylazo-2-acetonylpyrimidines occurs.

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. G. Ya. Remmenikov, I. A. Dyachenko, and V. V. Pirozhenko, Khim. Geterotsikl. Soedin., No. 1, 101 (1992).

    Google Scholar 

  2. A. L. Weis and H. C. van der Plas, Heterocycles, 24, 1433 (1986).

    Google Scholar 

  3. A. L. Weis, F. Frolow, and R. Viskautsan, J. Org. Chem., 51, 4623 (1986).

    Google Scholar 

  4. G. Ya. Remennikov, S. G. Vishnevskii, V. V. Pirozhenko, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 9, 1238 (1990).

    Google Scholar 

  5. A. Ya. Kaminskii, S. S. Gitis, L. L. Bagal, Yu. D. Grudtsyn, T. P. Ikher, L. V. Illarionova, and N. D. Stepanov, Zh. Org. Khim., 13, 803 (1977).

    Google Scholar 

  6. Ya. F. Freimanis, Chemistry of Enaminoketones, Enaminoamines, and Enaminothiones [in Russian], Zinatne, Riga (1974), p. 111.

    Google Scholar 

  7. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. II, No. 1, 1 (1987).

    Google Scholar 

  8. V. M. Cherkasov, G. Ya. Remennikov, A. A. Kisilenko, and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 2, 239 (1980).

    Google Scholar 

  9. V. M. Cherkasov, G. Ya. Remennikov, and E. A. Romanenko, Khim. Geterotsikl. Soedin., No. 10, 1389 (1978).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry and Petrochemistry, Ukrainian Academy of Sciences, 253660, Kiev

    G. Ya. Remennikiv, S. G. Vishnevskii, V. V. Pirozhenko, S. I. Vdovenko, V. M. Cherkasov, D. S. Yufit & Yu. T. Struchkov

  2. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, 117334, Moscow

    G. Ya. Remennikiv, S. G. Vishnevskii, V. V. Pirozhenko, S. I. Vdovenko, V. M. Cherkasov, D. S. Yufit & Yu. T. Struchkov

Authors
  1. G. Ya. Remennikiv
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Vishnevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Pirozhenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. I. Vdovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. M. Cherkasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. S. Yufit
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yu. T. Struchkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 10, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 215–223, February, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Remennikiv, G.Y., Vishnevskii, S.G., Pirozhenko, V.V. et al. Sigma-complexes in the pyrimidine series. 11. 5-arylazo-5-nitro-2,5- and -4,5-dihydro-pyrimidines from anionic sigma complexes of 5-nitropyrimidine. Chem Heterocycl Compd 29, 186–193 (1993). https://doi.org/10.1007/BF00531663

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00531663

Keywords

Search

Navigation