Skip to main content
SpringerLink
Log in

Nucleophilic substitution at the C(4) atom in series of functionally 4-substituted hexahydropyrimidine-2-thiones. Synthesis of 4-alkylthiohexahydropyrimidine-2-thiones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Nucleophilic substitution at the C(4) atom in 4-hydroxy(alkoxy)hexahydropyrimidine-2-thiones under the influence of alkanethiols in acidic, neutral, and basic media, as a result of which 4-alkylthiohexahydropyrimidine-2-thiones are formed, was studied. Hydrolysis and alcoholysis of the latter lead to the corresponding 4-hydroxy- or 4-alkoxyhexahydropyrimidine-2-thiones. The three-dimensional structures of the 4-alkylthiopyrimidines obtained were established by PMR spectroscopy, and it was shown that the stereoisomers with an axially oriented alkylthio group are thermodynamically more stable.

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. L. A. Ignatova, A. D. Shutalev, A. G. Shingareeva, S. F. Dymova, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 2, 260 (1985).

    Google Scholar 

  2. D. Beke, C. Szantay, and M. Beke-Barchai, Annalen, 635, 150 (1960).

    Google Scholar 

  3. A. M. Arnett, in: Modern Problems of Physical Organic Chemistry [Russian translation], Mir, Moscow (1967), p. 195.

    Google Scholar 

  4. A. Kirby, The Anomeric Effect of Oxygen-Containing Compounds [Russian translation], Mir, Moscow (1985), p. 94.

    Google Scholar 

  5. R. K. Ritchie and H. Spedding, Spectrochim. Acta, 26A, 9 (1970).

    Google Scholar 

  6. K. Dwarakanath and D. N. Sathyanarayana, Indian J. Chem., 18A, 302 (1979).

    Google Scholar 

  7. A. Gordon and R. Ford, The Chemist's Guide [Russian translation], Mir, Moscow (1976), p. 303.

    Google Scholar 

  8. H. W. Dias and M. R. Truter, Acta Cryst., 17, 937 (1964).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Fine Chemical Technology, 119831, Moscow

    L. A. Ignatova, A. D. Shutalev, M. T. Pagaev & B. V. Unkovskii

Authors
  1. L. A. Ignatova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. D. Shutalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. T. Pagaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. B. V. Unkovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 234–240, February, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ignatova, L.A., Shutalev, A.D., Pagaev, M.T. et al. Nucleophilic substitution at the C(4) atom in series of functionally 4-substituted hexahydropyrimidine-2-thiones. Synthesis of 4-alkylthiohexahydropyrimidine-2-thiones. Chem Heterocycl Compd 24, 197–203 (1988). https://doi.org/10.1007/BF00473332

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00473332

Keywords

Search

Navigation