Synthesis of Fluorine-Containing Imidazolidin-2-Ones, Glycolurils, and Hydantoins Based on Perfluorodiacetyl and Ureas*

Autor:	A. Ya. Zapevalov, V. I. Saloutin, M. I. Kodess, Oleg N. Chupakhin, Pavel A. Slepukhin, L. V. Saloutina
Rok vydání:	2014
Předmět:	chemistry.chemical_compound Trifluoromethyl chemistry Yield (chemistry) Organic Chemistry Nucleophilic substitution Urea Organic chemistry Fluorine containing Cis–trans isomerism
Zdroj:	Chemistry of Heterocyclic Compounds. 50:958-966
ISSN:	1573-8353 0009-3122
Popis:	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-(trifluoro-methyl)-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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f4bbbd7d700f2256134bfb85a03ddb2b https://doi.org/10.1007/s10593-014-1550-z Zobrazit plný text záznamu Plný text ve formátu PDF