Synthesis of fluorine-containing allantoins,hydantoins, and oxazolones from terminal perfluoroolefin oxides and urea |
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Authors: | L. V. Saloutina A. Ya. Zapevalov M. I. Kodess V. I. Saloutin O. N. Chupakhin |
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Affiliation: | 1.Postovskii Institute of Organic Synthesis, Ural Division,Russian Academy of Sciences,Yekaterinburg,Russia |
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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. |
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