THE INTERACTION OF THE 4-CARBOXYPHENYLGLYOXAL WITH N-HYDROXYUREA AND N-ALKOXY-N’-ALKYL(ARYL)UREAS. THE STUCTURE OF 5-(4-CARBOXYPHENYL)-4,5-DIHYDROXY-1-METHYL-3-PROPYLOXYIMIDAZOLIDIN-2-ONE
DOI:
https://doi.org/10.15421/jchemtech.v29i4.233171Keywords:
3-alkoxy-1,5-bis(aryl)-4,5-dihydroxyimidazolidin-2-ones; 3-alkoxy-1-alkyl-5-aryl-4,5-dihydroxyimidazolidin-2-ones; synthesis; structure.Abstract
Aim. The investigation of the reaction of 4-carboxyphenylglyoxal with N-hydroxyurea, different N-alkoxy-N’-arylureas and N-propyloxy-N’-methylurea in acetic acid medium and the product structure. Methods.1H and 13C NMR, mass spectra and XRD study. Results. 3-Alkoxy-4,5-dihydroxyimidazolidin-2-ones are the only products of N-alkoxy-N’-alkyl(aryl)ureas interaction with 4-carboxyphenylglyoxal. The possibility of obtaining such dominating products as 3-alkoxy-1-aryl-5-(4-carboxyphenyl)-4,5-dihydroxyimidazolidin-2-ones and 3-alkoxy-1-alkyl-5-(4-carboxyphenyl)-4,5-dihydroxyimidazolidin-2-ones with cis orientation of 4-HO- and 5-HO-groups to each other has been proved in the experimental way. The product structure was revealed by the 1H and 13C NMR, mass spectra and XRD study. Also the structure of 5-(4-carboxyphenyl)-4S,5S-dihydroxy-1-methyl-3-propyloxyimidazolidin-2-one is discussed in this article. In this compound the endocyclic C(2)–C(3) bond is elongated to 1.562(2) Å) as compared to the average length of C(sp3)–C(sp3) ordinary bond. The N(1) atom has almost planar configuration whereas the N(2) atom has pyramidal configuration. The N(1)–C(1) bond is shorter than the N(2)–C(1) bond. 4-Carboxyphenylglyoxal reacts with N-hydroxyurea in acetic acid at room temperature with the selective formation of 5-(4-carboxyphenyl)-3-hydroxyimidazolidine-2,4-dione. Conclusions. 4-Carboxyphenylglyoxal reacts with N-propyloxy-N’-methylurea and N-alkoxy-N-arylureas in acetic acid at room temperature selectively producing 5-(4-carboxyphenyl)-4,5-dihydroxy-1-methyl-3-propyloxyimidazolidin-2-one and 3-alkoxy-1-aryl-5-(4-carboxyphenyl)-4,5-dihydro-xyimidazolidin-2-ones with cis orientation of 4-HO- and 5-HO-groups towards each other. In the same conditions 4-carboxyphenylglyoxal interacts with N-hydroxyurea yielding only 5-(4-carboxyphenyl)-3-hydroxyimidazolidine-2,4-dione.
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