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Simple and efficient synthesis of trisubstituted imidazoles

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Chemistry of Heterocyclic Compounds Aims and scope

The thermally activated or microwave-induced one-pot three-component condensation of arylglyoxal hydrates, 1,3-dimethylbarbituric acid, and guanidine salts or methylisothiuronium hydroiodide gave respectively 2-amino-5-aryl- and 5-aryl-2-methylsulfanylimidazoles containing a 1,3-dimethylbarbituric acid residue. An unexpected course for the condensation was discovered in the case of guanidine hydrochloride, leading to 5-(2-aryl-2-oxoethyl)-1,3-dimethylbarbituric acids. 2-Amino-2-arylimidazoles under the conditions of such three-component condensation formed Michael adducts involving 5-(2-aryl-2- oxoethylidene)-1,3-dimethylbarbituric acids and the C-5 atom of the imidazole ring.

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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 & E. V. Vashchenko

Authors
  1. N. N. Kolos
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  2. N. V. Chechina
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  3. L. L. Zamigailo
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  4. E. V. Vashchenko
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Correspondence to N. N. Kolos.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 935-944, June, 2013.

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Kolos, N.N., Chechina, N.V., Zamigailo, L.L. et al. Simple and efficient synthesis of trisubstituted imidazoles. Chem Heterocycl Comp 49, 872–881 (2013). https://doi.org/10.1007/s10593-013-1321-2

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  • DOI: https://doi.org/10.1007/s10593-013-1321-2

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