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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    N. N. Kolos & N. V. Chechina

  2. Scientific-Technological Complex “Institute of Monocrystals”, National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv, 61001, Ukraine

    L. L. Zamigailo, I. V. Omel’chenko, O. V. Shishkin & E. V. Vashchenko

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  1. N. N. Kolos
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  2. L. L. Zamigailo
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  3. N. V. Chechina
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  4. I. V. Omel’chenko
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  5. O. V. Shishkin
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  6. E. V. Vashchenko
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Correspondence to N. N. Kolos.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1941-1947, December, 2012.

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Kolos, N.N., Zamigailo, L.L., Chechina, N.V. et al. Three-component condensation of 1,3-dimethyl-barbituric acid, arylglyoxals, and substituted thioureas. Chem Heterocycl Comp 48, 1817–1823 (2013). https://doi.org/10.1007/s10593-013-1214-4

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  • DOI: https://doi.org/10.1007/s10593-013-1214-4

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