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SYNTHESIS OF FLUORINE-CONTAINING IMIDAZOLIDIN-2-ONES, GLYCOLURILS, AND HYDANTOINS BASED ON PERFLUORODIACETYL AND UREAS

Л. В. Салоутина, А. Я. Запевалов, П. А. Слепухин, М. И. Кодесс, В. И. Салоутин, О. Н. Чупахин
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Abstract


The reactions of perfluorodiacetyl with urea, N,N'-dimethyl- and N,N'-diethylureas produced the cis and trans isomers of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones in 60-90% yields. The reaction of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with urea gave 1,5-bis-(trifluoromethyl)-2,4,6,8-tetraazobicyclo[3.3.0]octane-3,7-dione in 88% yield. The analogous reaction of 1,3-di-methyl- and 1,3-diethylimidazolidin-2-ones with urea, N,N'-dimethyl- and N,N'-diethylureas led to the formation of 5-hydroxy-1,3-dimethyl(diethyl)-5-trifluoromethylimidazolidine-2,4-diones (hydantoins) in 60-87% yields. The molecular structures of cis-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one, trans-4,5‑dihydroxy-1,3-dimethyl-4,5-bis(trifluoromethyl)imidazolidin-2‑one, and 5‑hydroxy-1,3-di-methyl-5-trifluoromethylimidazolidine-2,4-dione were studied by X-ray structural analysis.

How to Cite
Saloutina, L. V.; Zapevalov, A. Ya.; Slepukhin, P. A.; Kodess, M. I.; Saloutin, V. I.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2014, 50, 958. [Khim. Geterotsikl. Soedin. 2014, 1040.]

For this article in the English edition see DOI 10.1007/s10593-014-1550-z


Keywords


N,N'-diethylurea; 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones; N,N'-dimethylurea; glycolurils; hydantoins; perfluorodiacetyl; urea; cis, trans isomers; nucleophilic substitution

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