Skip to main content
SpringerLink
Log in

Lactam acetals and acid amides. 32. Lactim-lactam tautomerization of condensed 4-pyridones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The tautomeric properties of a number of condensed 4-pyridone derivatives were investigated. The existence of lactim-lactam tautomerization in this series of compounds was established by IR and UV spectroscopy. It is shown that when α substituents are present in the 4-pyridone molecule, both intramolecular electronic effects and the effect of substituents on solvation of one or another tautomeric form and, consequently, on the position of the equilibrium should be taken into account.

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

Literature cited

  1. V. G. Granik, S. S. Kiselev, N. P. Solov'eva, I. V. Persianova, M. K. Polievktov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 3, 344 (1980).

    Google Scholar 

  2. J. M. Elguero, C. Marzin, A. R. Katritzky, and P. Lindo, Tautomerism of Heterocycles. Advances in Heterocyclic Chemistry, Supplement 1, Academic Press, New York-San Francisco-London (1976).

    Google Scholar 

  3. L. N. Yakhontov (Jakhontov), D. M. Krasnokut-skaya, E. M. Peresleni, Yu. N. Sheinker, and M. V. Rubtsov, Tetrahedron, No. 10, 3325 (1966).

    Google Scholar 

  4. E. M. Peresleni, M. Ya. Uritskaya, V. A. Loginova, Yu. N. Sheinker, and L. N. Yakhontov, Dokl. Akad. Nauk SSSR,183, 1102 (1968).

    CAS  Google Scholar 

  5. V. G. Granik, E. M. Peresleni, O. Ya. Belyaeva, T. D. Zotova, O. S. Anisimova, R. G. Glushkov, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 6, 793 (1978).

    Google Scholar 

  6. P. Beak, F. Fry, J. Lee, and F. Steele, J. Am. Chem. Soc.,98, 171 (1976).

    Article  CAS  Google Scholar 

  7. Yu. N. Sheinker, Sb. Tr. Vses. Nauchno-Issled. Khim.-Farm. Inst.,2, 219 (1971).

    Google Scholar 

  8. L. N. Yakhontov, D. M. Krasnokut-skaya, E. M. Peresleni, Yu. N. Sheinker, and M. V. Rubtsov, Dokl. Akad. Nauk SSSR,172, 118 (1967).

    CAS  Google Scholar 

  9. P. Beak, J. B. Covington, and S. G. Smith, J. Am. Chem. Soc.,98, 8284 (1976).

    Article  CAS  Google Scholar 

  10. A. M. Zhidkova, V. G. Granik, R. G. Glushkov, T. F. Vlasova, O. S. Anisimova, T. A. Gus'kova, and G. N. Pershin, Khim. Geterotsikl. Soedin., No. 5, 670 (1974).

    Google Scholar 

  11. I. B. Marchenko, V. G. Granik, R. G. Glushkov, E. M. Peresleni, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farm. Zh., No. 11, 49 (1976).

    Google Scholar 

  12. V. G. Granik, A. M. Zhidkova, S. S. Kiselev, R. G. Glushkov, A. I. Polezhaeva, and M. D. Mashkovskii, Khim.-Farm. Zh., No. 7, 66 (1978).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119021, Moscow

    V. G. Granik, E. M. Peresleni, T. D. Kurochkina, A. M. Zhidkova, N. B. Marchenko, R. G. Glushkov & Yu. N. Sheinker

Authors
  1. V. G. Granik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. M. Peresleni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. D. Kurochkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. M. Zhidkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. B. Marchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. R. G. Glushkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yu. N. Sheinker
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication 31.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 349–353, March, 1980.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Granik, V.G., Peresleni, E.M., Kurochkina, T.D. et al. Lactam acetals and acid amides. 32. Lactim-lactam tautomerization of condensed 4-pyridones. Chem Heterocycl Compd 16, 260–264 (1980). https://doi.org/10.1007/BF02401723

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02401723

Keywords

Search

Navigation