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

被引：0

作者：

L. V. Saloutina

A. Ya. Zapevalov

P. A. Slepukhin

M. I. Kodess

V. I. Saloutin

O. N. Chupakhin

机构：

[1] Russian Academy of Sciences,I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch

来源：

Chemistry of Heterocyclic Compounds | 2014年 / 50卷

关键词：

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

D O I：

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中图分类号：

学科分类号：

摘要：

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.

引用

页码：958 / 966

页数：8

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