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ANDREA PACE

Synthesis of fluorinated 1,2,4-oxadiazin-6-ones through ANRORC rearrangement of 1,2,4-oxadiazoles

  • Authors: Palumbo Piccionello, A; Pace, A; Buscemi, S; Vivona, N; Giorgi, G
  • Publication year: 2009
  • Type: Articolo in rivista (Articolo in rivista)
  • Key words: Oxadiazoles, Oxadiazinones, ANRORC rearrangement, Fluorinated heterocycles
  • OA Link: http://hdl.handle.net/10447/34826

Abstract

The reaction of 3-ethoxycarbonyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydroxylamines has been investigated, evidencing the possibility of competitive reaction paths. Nucleophilic addition of hydroxylamine to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring-opening and ring-closure with enlargement, leads to high yield and in very mild experimental conditions to the formation of 5-hydroxyamino-3-perfluoroalkyl-6H-1,2,4-oxadiazin-6-ones, one of these presenting water gelation ability. In turn, reactions with N-methylhydroxylamine lead the exclusive formation of 4-perfluoroacylamino- 2-methyl-2H-1,2,5-oxadiazol-3-ones through the well known Boulton–Katritzky rearrangement.