SIMPLE AND EFFICIENT SYNTHESIS OF TRISUBSTITUTED IMIDAZOLES
DOI:
https://doi.org/10.1007/381Keywords:
5-(2-amino-5-arylimidazol-4-yl)-1, 3-dimethylbarbituric acids, arylglyoxals, 5-(5-aryl-2 methyl-sulfanylimidazol-4-yl)-1, 5-(2-aryl-2-oxoethyl)-1, 1, 3-dimethylbarbituric acid, guanidine salts, methylisothiuronium hydroiodide, Michael adductsAbstract
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.
Authors: N. N. Kolos, N. V. Chechina, L. L. Zamigailo, and E. V. Vashchenko.
English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (6), pp 872-881
