S 98 Synthesis of fluorine-containing allantoins, hydantoins, and oxazolones from terminal perfluoroolefin oxides and urea / L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2012. - Vol.48, №3. - С. 387-393 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALLANTOINS -- HYDANTOINS -- OXAZOLONES Аннотация: 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 \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2012, 48 (3), 387-393.pdf |