Synthesis of Fluorine-Containing Allantoins, Hydantoins, and Oxazolones from Terminal Perfluoroolefin Oxides and Urea

摘要

1,2-Epoxyoctafluorobutane reacted with urea in DMSO and aqueous DMSO, dioxane, and aceto-nitrile to give 40-12% of 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione. 5-Hydroxy-5-tridecafluoro-hexylimidazolidine-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 JV-(l-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.