Synthesis of Fluorine-Containing Imidazolidin-2-Ones, Glycolurils, and Hydantoins Based on Perfluorodiacetyl and Ureas / Saloutina L. V.,Zapevalov A. Ya.,Slepukhin P. A.,Kodess M. I.,Saloutin V. I.,Chupakhin O. N. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2014. - V. 50, l. 7. - P. 958-966.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

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-(trifluoro-methyl)-2,4,6,8-tetraazobicyclo{[}3.3.0]octane-3,7-di one 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-dione s (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.

Author keywords:

N,N `-diethylurea; 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones; N,N `-dimethyl-urea; glycolurils; hydantoins; perfluorodiacetyl; urea; cis,trans isomers; nucleophilic substitution TRIFLUOROPYRUVIC ACID HYDRATE; HETEROCYCLIC SYNTHESIS; DERIVATIVES

DOI:

10.1007/s10593-014-1550-z

Web of Science ID:

ISI:000344092000005

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	TRIFLUOROPYRUVIC ACID HYDRATE; HETEROCYCLIC SYNTHESIS; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	Ural Branch of Russian Academy of Sciences {[}12-P-3-1030, 12-M-23-2054]; Grants Council of the President of the Russian Federation {[}NSh-3656.2014.3]
Funding-Text	The work received financial support from the Ural Branch of Russian Academy of Sciences (projects 12-P-3-1030 and 12-M-23-2054) and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).
Number-of-Cited-References	24
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	9
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AS2EG