A series of 6-substituted fluorinated indazoles has been obtained through an ANRORC-like rearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5-tetrafluorophenyl-1,2,4-oxadiazoles with 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 fluorinated indazoles in high yield under mild experimental conditions. Functionalization of the C(6) in the final indazole nucleus was preliminarily achieved through a nucleophilic aromatic substitution on the starting 5-pentafluorophenyl-1,2,4-oxadiazole.
|Data di pubblicazione:||2006|
|Titolo:||Synthesis of fluorinated indazoles through ANRORC-like rearrangement of 1,2,4-oxadiazoles with hydrazine|
|Autori:||PALUMBO PICCIONELLO A; PACE A; PIBIRI I; BUSCEMI S; VIVONA N|
|Tipologia:||Articolo su rivista|
|Citazione:||PALUMBO PICCIONELLO A, PACE A, PIBIRI I, BUSCEMI S, & VIVONA N (2006). Synthesis of fluorinated indazoles through ANRORC-like rearrangement of 1,2,4-oxadiazoles with hydrazine. TETRAHEDRON, 62, 8792-8797.|
|Digital Object Identifier (DOI):||10.1016/j.tet.2006.06.100|
|Appare nelle tipologie:||01 - Articolo su rivista|