Advertisement

Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 823–829 | Cite as

New data on the alkylation of cyclic thioureas with α-halo-carboxylic acids and their esters. 3. Alkylation of butylenethioureas

  • P. M. Kushakova
  • S. M. Ramsh
  • V. V. Lifontova
  • A. V. Garabadgiu
  • L. N. Belobrzhetskaja Kosta
Article

Abstract

The reactions of 1,3-diazepane-2-thione with α-halocarboxylic acids and their esters have been studied in detail. On alkylation of butylenethiourea with chloroacetic acid and ethyl chloro(bromo)acetate in anhydrous acetone at room temperature the hydrogen chloride of the S-carboxymethyl and the hydrogen halides of the S-ethoxycarbonylmethyl derivatives respectively of the cyclic substrate were formed initially. When butylenethiourea was alkylated with chloroacetic acid in boiling ethanol in the presence of sodium acetate the neutral (zwitterionic) form of its S-carboxymethyl derivative was also formed. Our results and the literature data on the alkylation of 5-, 6-, and 7-membered cyclic thioureas with α-halocarboxylic acids and their esters have been reviewed and interpreted.

Keywords

1,3-diazepane-2-thione (butylenethiourea) reactions with α-halocarboxylic acids and their esters 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    P. M. Kushakova, A. I. Yulisova, S. M. Ramsh, and A. V. Garabadgiu, Khim. Geterotsikl. Soedin., 593 (2006).Google Scholar
  2. 2.
    V. S. Chadha, H. S. Chaudhary, and H. K. Pujari, Aust J. Chem., 22, 2697 (1969).CrossRefGoogle Scholar
  3. 3.
    E. Campaigne and M. C. Wani, J. Org. Chem., 29, 1715 (1964).Google Scholar
  4. 4.
    P. M. Kushakova, S. M. Ramsh, and A. V. Garabadgiu, Khim. Geterotsikl. Soedin., 250 (2006).Google Scholar
  5. 5.
    J. March, Organic Chemistry [Russian translation], Mir, Moscow, Vol. 2, 340 (1988).Google Scholar
  6. 6.
    V. M. Potapov (editor), Organikum [in Russian], Mir, Moscow, Vol. 2, 335 (1979).Google Scholar
  7. 7.
    B. A. Kazanskii (editor), Synthesis of Organic Preparations [Russian translation], Izd-vo Inostr. Lit., Moscow, Vol. 5, 574 (1953).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • P. M. Kushakova
    • 1
  • S. M. Ramsh
    • 1
  • V. V. Lifontova
    • 1
  • A. V. Garabadgiu
    • 1
  • L. N. Belobrzhetskaja Kosta
    • 2
  1. 1.St. Petersburg State Technological InstituteSt. PetersburgRussia
  2. 2.Genoa State UniversityGenoaItaly

Personalised recommendations