Skip to main content
SpringerLink
Log in

Investigation of the reactivities and tautomerism of azolidines. 46. PMR spectra and structures of the products of hydroxymethylation and aminomethylation of 2-imino-5-arylidene-4-thiazolidinones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

On the basis of dual reactivity concepts, it is shown that the hydroxy- and amino-methylation of ambifunctional 2-imino-5-R-benzylidene-4-thiazolidinones (R = H, p-Cl, p-OCH3, p-Br, and p-F) should be directed to the same reaction center. On the basis of PMR spectroscopic data, it was confirmed that this center is the exocyclic nitrogen atom. It was established that 2-piperidinomethylamino-5-R-benzyli-dene-4-thiazolinones (R = H, p-Cl, p-N02, p-OCH3, p-Br, and p-F) exist in d6-DMSO primarily in the form of E conformers of the amino form. The E conformers of the latter compounds are chelate structures with an intramolecular hydrogen bond.

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. A. I. Ginak, K. A. V'yunov, and S. M. Ramsh, Zh. Org. Khim., 19, 212 (1983).

    Google Scholar 

  2. S. Yu. Solov'eva-Yavits, S. M. Ramsh, N. A. Smorygo, A. I. Ginak, and E. G. Sochilin, Khim. Geterotsikl. Soedin., No. 7, 929 (1980).

    Google Scholar 

  3. S. A. Shevelev, Usp. Khim., 39, 1773 (1970).

    Google Scholar 

  4. A. F. Halasa and G. E.P. Smith, J. Org. Chem., 36, 636 (1971).

    Google Scholar 

  5. H. Becker, Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1977), pp. 300, 301, 394.

    Google Scholar 

  6. V. A. Palm, Fundamentals of the Quantitative Theory of Organic Reactions [in Russian], Khimiya, Leningrad (1977), p. 291.

    Google Scholar 

  7. O. O. Orazi and R. A. Corral, Tetrahedron, 15, 93 (1961).

    Google Scholar 

  8. O. Exner, Chem. Listy, 67, 699 (1973).

    Google Scholar 

  9. R. Silverstein, G. Bassler, and T. Morrill, Spectrophotometric Identification of Organic Compounds, Wiley (1974).

  10. L. Gendelman, Monatsh. Chem., 43, 537 (1922).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lensovet Leningrad Technological Institute, 198013, Leningrad

    S. M. Ramsh, S. Yu. Solov'eva & A. I. Ginak

Authors
  1. S. M. Ramsh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Yu. Solov'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Ginak
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication 45.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 928–932, July, 1983,

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ramsh, S.M., Solov'eva, S.Y. & Ginak, A.I. Investigation of the reactivities and tautomerism of azolidines. 46. PMR spectra and structures of the products of hydroxymethylation and aminomethylation of 2-imino-5-arylidene-4-thiazolidinones. Chem Heterocycl Compd 19, 745–749 (1983). https://doi.org/10.1007/BF00506099

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506099

Keywords

Search

Navigation