Three-component condensation of 1,3-dimethyl-barbituric acid, arylglyoxals, and substituted thioureas

4-Aryl-2-methylaminothiazoles and 5-aryl-2-mercapto-1-methylimidazoles, containing a fragment of 1,3-dimethylbarbituric acid, have been synthesized by the one-pot three-component condensation of 1,3-dimethylbarbituric acid, arylglyoxal hydrates, and N -methylthiourea. The analogous reaction involvin...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2013-03, Vol.48 (12), p.1817-1823
Main Authors: Kolos, N. N., Zamigailo, L. L., Chechina, N. V., Omel’chenko, I. V., Shishkin, O. V., Vashchenko, E. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:4-Aryl-2-methylaminothiazoles and 5-aryl-2-mercapto-1-methylimidazoles, containing a fragment of 1,3-dimethylbarbituric acid, have been synthesized by the one-pot three-component condensation of 1,3-dimethylbarbituric acid, arylglyoxal hydrates, and N -methylthiourea. The analogous reaction involving N -arylthioureas proceeds regioselectively with the formation of 4-aryl-2-arylaminothiazoles. It was established that in the crystalline state 5-aryl-2-mercaptoimidazoles exist in the imidazoline-2-thione form.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1214-4