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ANDREA PACE

An ANRORC approach to the synthesis of perfluoroalkylated 1,2,4-triazole-carboxamides

  • Authors: PALUMBO PICCIONELLO, A.; Pace, A.; Buscemi, S.; Vivona, N.
  • Publication year: 2009
  • Type: Articolo in rivista (Articolo in rivista)
  • Key words: Fluorinated heterocycles, triazole, oxadiazole, ANRORC rearrangements
  • OA Link: http://hdl.handle.net/10447/34825

Abstract

A series of perfluoroalkyl-1,2,4-triazole-carboxamides has been obtained through an ANRORClike rearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5- perfluoroalkyl-1,2,4-oxadiazole-3-carboxamides with methylhydrazine or hydrazine. The initial addition of the bidentate nucleophile to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring opening and ring closure, leads to the formation of triazoles in good yield under mild experimental conditions. In some cases, a competitive ANRORC-enlargement reaction to form 1,2,4-triazin-6-ones was also observed. Obtained carboxamidotriazoles have also been explored as precursors for the synthesis of 3(5)-perfluoroalkyl-1,2,4-triazoles