THREE-COMPONENT CONDENSATION OF 1,3-DIMETHYLBARBITURIC ACID, ARYLGLYOXALS, AND SUBSTITUTED THIOUREAS

Authors

  • Н. Н. Колос V. N. Karazin Kharkiv National University
  • Л. Л. Замигайло Scientific-Technological Complex "Institute of Monocrystals"
  • Н. В. Чечина V. N. Karazin Kharkiv National University
  • И. В. Омельченко Scientific-Technological Complex "Institute of Monocrystals"
  • О. В. Шишкин Scientific-Technological Complex "Institute of Monocrystals"
  • Е. В. Ващенко Scientific-Technological Complex "Institute of Monocrystals"

DOI:

https://doi.org/10.1007/857

Keywords:

arylglyoxals, 5-(4-aryl-2-(methylamino)thiazol-5-yl)-6-hydroxy-1, 3-dimethylpyrimidine-2, 4 diones, 5-(5-aryl-1-methyl-2-thioxoimidazolidin-4-ylidene)-1, 4, 6-triones, 1, 3 dimethylbarbituric acid, N-methyl(aryl)thioureas

Abstract

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.

Authors: N. N. Kolos, L. L. Zamigailo, N. V. Chechina, I. V. Omel'chenko, O. V. Shishkin, and E. V. Vashchenko

English Translation in Chemistry of Heterocyclic Compounds, 2013, 48 (12), pp 1817-1823

http://link.springer.com/article/10.1007/s10593-013-1214-4

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Published

2013-08-20

Issue

No. 12 (2012)

Section

Original Papers