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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 4, pp 520–529 | Cite as

New data on the alkylation of cyclic thioureas with á-halocarboxylic acids and their esters. 2. Alkylation of tetrahydropyrimidine-2(1h)-thione and 5,5-dimethyltetrahydropyrimidine-2(1h)-thione

  • P. M. Kushakova
  • A. I. Yulisova
  • S. M. Ramsh
  • A. V. Garabadgiu
Article

Abstract

In the absence of bases all the attempted variations for the alkylation of tetrahydropyrimidine-2(1H)-thione with á-halocarboxylic acids gave only the bicyclic product-2-R-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one hydrohalide. However the hydrohalide of the “ open” S-ethoxycarbonyl derivative of propyleneisothiourea can be obtained by treatment of tetrahydropyrimidine-2(1H)-thione with ethyl chloro-or bromoacetate in anhydrous acetone at room temperature. Alkylation of 5,5-dimethyltetrahydro-2(1H)-pyrimidinethione with chloro-or bromoacetic acid in anhydrous acetone at room temperature gave the hydrohalide of the “open” S-carboxymethyl derivative of dimethylpropyleneisothiourea. All remaining variations for the alkylation of this substrate with á-halocarboxylic acids or their esters gave only the corresponding bicyclic compounds-the hydrohalide of 2-R-6,6-dimethyl-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one-independently of the reaction conditions.

Keywords

5,5-dimethyltetrahydro-2(1H)-pyrimidinethione tetrahydropyrimidine-2(1H)-thione (propylenethiourea) reactions with á-halocarboxylic acids and their esters 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • P. M. Kushakova
    • 1
  • A. I. Yulisova
    • 1
  • S. M. Ramsh
    • 1
  • A. V. Garabadgiu
    • 1
  1. 1.St. Petersburg State Technological UniversitySt. PetersburgRussia

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