Synthesis of new substituted 5-methyl-3,5-diphenylimidazolidine-2,4-diones from substituted 1-(1-cyanoethyl-1-phenyl)-3-phenylureas

doi:10.1002/JHET.5570420523

Paper

Synthesis of new substituted 5-methyl-3,5-diphenylimidazolidine-2,4-diones from substituted 1-(1-cyanoethyl-1-phenyl)-3-phenylureas

Published Jul 1, 2005 · M. Sedlák, Roman Keder, J. Hanusek

Journal of Heterocyclic Chemistry

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Abstract

The reaction of substituted phenyl isocyanates with 2-amino-2-phenylpropanenitrile and 2-amino-2-(4-nitrophenyl)propanenitrile has been used to prepare substituted 1-(1-cyanoethyl-1-phenyl)-3-phenylureas. In anhydrous phosphoric acid the first products to be formed from 1-(1-cyanoethyl-1-phenyl)-3-phenylureas are phosphates of 4-methyl-4-phenyl-2-phenylimino-5-imino-4,5-dihydro-1,3-oxazoles, which on subsequent hydrolysis give the respective ureidocarboxylic acids. On prolongation of the reaction time, the phosphates of 4-methyl-4-phenyl-2-phenylimino-5-imino-4,5-dihydro-1,3-oxazoles rearrange to give phosphates of 5-methyl-4-imino-3,5-diphenylimidazolidin-2-ones, and these are subsequently hydrolysed to the respective substituted 5-methyl-3,5-diphenylimidazolidin-2,4-diones. The ureidocarboxylic acids were also prepared by alkaline hydrolysis of 5-methyl-3,5-diphenylimidazolidin-2,4-diones. The 5-methyl-3,5-diphenylimidazolidin-2,4-diones and ureidocarboxylic acids were characterised by their 1H and 13C NMR spectra. Structure of the 5-methyl-5-(4-nitrophenyl)-3-phenylimidazolidine-2,4-dione was verified by X-ray diffraction. The alkaline hydrolysis of individual imidazolidine-2,4-diones was studies spectrophoto-metrically in sodium hydroxide solutions at 25 °C. The rate-limiting step of the base catalysed hydrolysis consists in decomposition of the tetrahedral intermediate. The reaction is faster if electron-acceptor sub-stituents are present in the 3-phenyl group of imidazolidine-2,4-dione cycle. The pKa values of individual 5-methyl-3,5-diphenylimidazolidine-2,4-diones have been determined kinetically.

Study Snapshot

Substituted 5-methyl-3,5-diphenylimidazolidin-2,4-diones can be synthesized from 1-(1-cyanoethyl-1-phenyl)-3-phenylureas, resulting in ureidocarboxylic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of new substituted 5-methyl-3,5-diphenylimidazolidine-2,4-diones from substituted 1-(1-cyanoethyl-1-phenyl)-3-phenylureas

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Citations

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Imidazole chemistry has advanced significantly since 1995, with significant advances in reactivity, synthesis, and applications.