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 |
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Authors: | P M Kushakova A I Yulisova S M Ramsh A V Garabadgiu |
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Institution: | (1) St. Petersburg State Technological University, St. Petersburg, 198013, Russia |
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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]thiazolo3,2-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]thiazolo3,2-a]pyrimidin-3(2H)-one-independently
of the reaction conditions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, 593–604, April, 2006. |
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Keywords: | 5 5-dimethyltetrahydro-2(1H)-pyrimidinethione tetrahydropyrimidine-2(1H)-thione (propylenethiourea) reactions with á-halocarboxylic acids and their esters |
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