NEW DATA ON THE ALKYLATION OF CYCLIC THIOUREAS WITH α-HALOCARBOXYLIC ACIDS AND THEIR ESTERS. 3. ALKYLATION OF BUTYLENETHIOUREAS

Authors

  • П. М. Кушакова St. Petersburg State Technological Institute, St. Petersburg 198013
  • С. М. Рамш St. Petersburg State Technological Institute, St. Petersburg 198013
  • В. В. Лифонтова St. Petersburg State Technological Institute, St. Petersburg 198013
  • А. В. Гарабаджиу St. Petersburg State Technological Institute, St. Petersburg 198013
  • Л. Н. Белобржецкая Коста Genoa State University, Genoa

DOI:

https://doi.org/10.1007/7962

Keywords:

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

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.

How to Cite
Kushakova, P. M.; Ramsh, S. M.; Lifontova, V. V.; Garabadgiu, A. V.; Belobrzhetskaja Kosta, L. N.  Chem. Heterocycl. Compd. 2006, 42, 823. [Khim. Geterotsikl. Soedin. 2006, 940.]

For this article in the English edition, see DOI 10.1007/s10593-006-0168-1


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Published

2023-08-15

Issue

No. 6 (2006)

Section

Original Papers