Synthesis of Fluorine-Containing Allantoins, Hydantoins, and Oxazolones from Terminal Perfluoroolefin Oxides and Urea / Saloutina L. V.,Zapevalov A. Ya.,Kodess M. I.,Saloutin V. I.,Chupakhin O. N. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2012. - V. 48, l. 3. - P. 387-393.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

1,2-Epoxyoctafluorobutane reacted with urea in DMSO and aqueous DMSO, dioxane, and acetonitrile to give 40-42\% of 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione. 5-Hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione was formed in 54\% yield in analogous reaction of 1,2-epoxytridecafluorooctane with urea in aqueous DMSO. The reactions of 1,2-epoxyoctafluorobutane and 1,2-epoxytridecafluorooctane with urea in anhydrous dioxane and acetonitrile unexpectedly afforded heterocyclization products, 2-amino-5-fluoro-5-perfluoroalkyloxazol-4(5H)-ones (yield 11-82\%). Fluorine-containing allantoin, 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (yield 19\%), and N-(1-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)-urea (yield 46\%) were synthesized for the first time by reaction of 1,2-epoxytridecafluoroctane with urea in DMSO and aqueous DMSO.

Author keywords:

нет данных

DOI:

10.1134/S1070428012030098

Web of Science ID:

ISI:000303682700009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	Council for Grants at the President of the Russian Federation {[}NSh-5505.2012.3]; Ural Division of the Russian Academy of Sciences {[}12-P-3-1030, 12-T-3-1025]
Funding-Text	This study was performed under financial support by the Council for Grants at the President of the Russian Federation (project no. NSh-5505.2012.3) and by the Ural Division of the Russian Academy of Sciences (project nos. 12-P-3-1030, 12-T-3-1025).
Number-of-Cited-References	22
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	5
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	937TV