Skip to main content
SpringerLink
Log in

Nucleophilic substitution or dipolar 1,3-cycloaddition in reactions of cyanamide with 4-arylpyrimidine 1-oxides

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Pyrimidine 1-oxides with cyanamide afforded 2-ureidopyrimidines as the result of the nucleophilic substitution of hydrogen, whereas the formation of similar 2-trichloroacetylaminopyrimidines occurs as dipolar 1,3-cycloaddition of the same oxides to trichloroacetonitrile under much more drastic conditions and in lower yields.

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. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 2000, 1128 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1122].

    Google Scholar 

  2. M. A. Kirilova, I. A. Maretina, and A. A. Petrov, Zh. Org. Khim., 1971, 7, 14 [J. Org. Chem. USSR, 1971, 7 (Engl. Transl.)].

    Google Scholar 

  3. G. Seitz and R. John, Chem. Ber., 1989, 122, 1381.

    Google Scholar 

  4. G. Seitz and X. G. Yang, Arch. Pharm., 1991, 324, 803.

    Google Scholar 

  5. H. Yamanaka, S. Nitsuma, T. Sakamoto, and M. Mizugaki, Heterocycles, 1976, 5, 255.

    Google Scholar 

  6. H. Yamanaka, S. Nitsuma, T. Sakamoto, and M. Mizugaki, Chem. Pharm. Bull., 1979, 27, 2291.

    Google Scholar 

  7. Yu. A. Azev, H. Neunhoeffer, and S. V. Shorshnev, Mendeleev Commun., 1996, 116.

  8. D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Adv. Heterocycl. Chem., 2002, 82, 261.

    Google Scholar 

  9. G. A. Shvekhgeimer, Khim. Geterotsikl. Soedin., 1993, 1443 [Chem. Heterocycl. Compd., 1993, 29 (Engl. Transl.)].

  10. V. F. Sedova, A. S. Lisitsyn, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1978, 1392 [Chem. Heterocycl. Compd., 1978, 14 (Engl. Transl.)].

    Google Scholar 

  11. W. E. Parham, J. F. Dooley, M. K. Meilahn, and J. W. Greidanus, J. Org. Chem., 1969, 34, 1474.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ural State Technical University, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    A. M. Prokhorov, D. N. Kozhevnikov & V. L. Rusinov

  2. Institute of Organic Synthesis, [Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    O. N. Chupakhin

Authors
  1. A. M. Prokhorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. N. Kozhevnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Prokhorov, A.M., Kozhevnikov, D.N., Rusinov, V.L. et al. Nucleophilic substitution or dipolar 1,3-cycloaddition in reactions of cyanamide with 4-arylpyrimidine 1-oxides. Russian Chemical Bulletin 52, 1195–1197 (2003). https://doi.org/10.1023/A:1024729912415

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1024729912415

Search

Navigation