Synthesis of fluorinated 1,2,4-oxadiazin-6-ones through ANRORC rearrangement of 1,2,4-oxadiazoles
作者： Antonio Palumbo Piccionello , Andrea Pace , Silvestre Buscemi , Nicolò Vivona , Gianluca Giorgi
DOI: 10.1016/J.TETLET.2009.01.071
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摘要: Abstract The reaction of 3-ethoxycarbonyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydroxylamines has been investigated, evidencing the possibility competitive paths. Nucleophilic addition hydroxylamine to electrophilic C(5) 1,2,4-oxadiazole ring, followed by ring-opening and ring-closure enlargement, leads high yield in very mild experimental conditions formation 5-hydroxyamino-3-perfluoroalkyl-6 H -1,2,4-oxadiazin-6-ones, one these presenting water gelation ability. In turn, reactions N -methylhydroxylamine lead exclusive 4-perfluoroacylamino-2-methyl-2 -1,2,5-oxadiazol-3-ones through well known Boulton–Katritzky rearrangement.
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