Novel route of the reaction of trifluoromethyl-containing N-methyl(4-ethoxyphenyl)imidazolidin-2-ones with urea / Saloutina L. V.,Zapevalov A. Ya.,Slepukhin P. A.,Kodess M. I.,Saloutin V. I.,Chupakhin O. N. // RUSSIAN CHEMICAL BULLETIN. - 2016. - V. 65, l. 2. - P. 473-478.

ISSN/EISSN:

1066-5285 / 1573-9171

Type:

Article

Abstract:

The reactions of perfluorobiacetyl with N-(4-ethoxyphenyl)- and N-methylurea afforded cis- and trans-isomers of 1-methyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one and 1-(4-ethoxyphenyl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2- one in a yield of similar to 60-75\%. N-Alkyl(aryl)bis(trifluoromethyl)imidazooxazoles were obtained as unexpected products in the reaction of 1-alkyl(aryl)-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with urea in dimethylacetamide. The reaction is accompanied by the rearrangement of imidazolidin-2-ones to N-alkyl(aryl)-5,5-bis(trifluoromethyl)hydantoins with CF3 group migration from position 5 to position 4 of the starting heterocycle. A similar rearrangement is observed on boiling of the studied imidazolidin-2-ones in dimethylacetamide. The molecular structures of 3-(4-ethoxyphenyl)-5,5-bis(trifluoromethyl)imidazolidine-2,4-dione and 6-(4-ethoxyphenyl)-3a,6a-bis(trifluoromethyl)tetrahydroimidazo{[}4,5-d]o xazole-2,5-dione were studied by X-ray diffraction analysis.

Author keywords:

perfluorobiacetyl; N-(4-ethoxyphenyl)urea; N-methylurea; urea; 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones; cis- and trans-isomers; imidazooxazoles; hydantoins; X-ray diffraction analysi HYDANTOINS

DOI:

10.1007/s11172-016-1324-0

Web of Science ID:

ISI:000387600700019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-9171
Keywords-Plus	HYDANTOINS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	fc403@ios.uran.ru
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}15-21-3-5]; Council on Grants of the President of the Russian Federation (Program for State Support of Leading Scientific Schools of the Russian Federation) {[}NSh-8922.2016.3]
Funding-Text	This work was financially supported by the Ural Branch of the Russian Academy of Sciences (Project No. 15-21-3-5) and the Council on Grants of the President of the Russian Federation (Program for State Support of Leading Scientific Schools of the Russian Federation, Grant NSh-8922.2016.3).
Number-of-Cited-References	18
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	EB7WB