NOVEL ALKYLATIONS OF CYCLIC THIOUREAS BY α-HALOCARBOXYLIC ACIDS AND THEIR ESTERS. 4. ALKYLATION OF 1-METHYLTETRAHYDROPYRIMIDINE-2(1H)-THIONE

Authors

  • П. М. Кушакова St. Petersburg State Technical University, St. Petersburg 198013
  • Ю. В. Басан St. Petersburg State Technical University, St. Petersburg 198013
  • А. И. Юлисова St. Petersburg State Technical University, St. Petersburg 198013
  • В. В. Лифонтова St. Petersburg State Technical University, St. Petersburg 198013
  • С. М. Рамш St. Petersburg State Technical University, St. Petersburg 198013
  • А. В. Гарабаджиу St. Petersburg State Technical University, St. Petersburg 198013
  • Л. Н. Белобржецкая Коста Genoa State University, Genoa

DOI:

https://doi.org/10.1007/7847

Keywords:

1-methyltetrahydropyrimidine-2(1H)-thione (N-methylpropylenethiourea), alkylation with chloro and bromoacetic acids and their esters

Abstract

Alkylation of 1-methyltetrahydropyrimidine-2(1H)-thione (N-methylpropylenethiourea) with chloro- and bromoacetic acids and their esters have given the 8-methyl-3-oxo-2,3,6,7-tetrahydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-8-ium chloride or  bromide. The former is readily hydrolyzed in 95% ethanol to 3-[(3-methylamino)propyl]-1,3-thiazolidine-2,4-dione hydrochloride while the second is more stable towards hydrolysis such that the corresponding hydrobromide is not  separated. A paradoxical trend in the extent of the hydrolysis decreasing with  the content of the water in the alcoholic solution comes to a complete stop in water. A possible explanation of this phenomenon is given.

How to Cite
Kushakova, P. M.; Basan, Yu. V.; Yulisova, A. I.; Lifontova, V. V.; Ramsh, S. M.; Garabadgiu, A. V.; Belobrzeckaja Costa, L. N.  Chem. Heterocycl. Compd. 2006, 42, 1078. [Khim. Geterotsikl. Soedin. 2006, 1242.]

For this article in the English edition see DOI 10.1007/s10593-006-0206-z


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Published

2023-05-26

Issue

No. 8 (2006)

Section

Original Papers