SYNTHESIS OF FLUORINE-CONTAINING IMIDAZOLIDIN-2-ONES, GLYCOLURILS, AND HYDANTOINS BASED ON PERFLUORODIACETYL AND UREAS

Authors

  • Л. В. Салоутина I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science
  • А. Я. Запевалов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science
  • П. А. Слепухин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science
  • М. И. Кодесс I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science
  • В. И. Салоутин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science
  • О. Н. Чупахин I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

DOI:

https://doi.org/10.1007/1675

Keywords:

N, N'-diethylurea, 4, 5-dihydroxy-4, 5-bis(trifluoromethyl)imidazolidin-2-ones, N'-dimethylurea, glycolurils, hydantoins, perfluorodiacetyl, urea, cis, trans isomers, nucleophilic substitution

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-(trifluoromethyl)-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.

How to Cite
Saloutina, L. V.; Zapevalov, A. Ya.; Slepukhin, P. A.; Kodess, M. I.; Saloutin, V. I.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2014, 50, 958. [Khim. Geterotsikl. Soedin. 2014, 1040.]

For this article in the English edition see DOI 10.1007/s10593-014-1550-z

Author Biographies

Л. В. Салоутина, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Людмила Васильевна Салоутина

лаборатория фторорганических соединений, научный сотрудник, к.х.н.

А. Я. Запевалов, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Александр Яковлевич Запевалов

лаборатория фторорганических соединений, ведущий научный сотрудник, д.х.н.

П. А. Слепухин, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Павел Александрович Слепухин

Руководитель группы РСА, с.н.с., к.х.н.

М. И. Кодесс, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Михаил Исаакович Кодесс

Зав. лаб., к.х.н.

В. И. Салоутин, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Виктор Иванович Салоутин

Зав. лабораторией, д.х.н., профессор

О. Н. Чупахин, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Science

Олег Николаевич Чупахин

научный руководитель института, академик РАН

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Published

2014-07-21

Issue

No. 7 (2014)

Section

Original Papers