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.

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(37), 8792-8797 [10.1016/j.tet.2006.06.100].

Synthesis of fluorinated indazoles through ANRORC-like rearrangement of 1,2,4-oxadiazoles with hydrazine

PALUMBO PICCIONELLO, Antonio;PACE, Andrea;PIBIRI, Ivana;BUSCEMI, Silvestre;VIVONA, Nicolo'
2006-01-01

Abstract

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.
2006
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(37), 8792-8797 [10.1016/j.tet.2006.06.100].
File in questo prodotto:
File Dimensione Formato  
1-s2.0-S0040402006010581-main.pdf

Solo gestori archvio

Dimensione 222.47 kB
Formato Adobe PDF
222.47 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/22316
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 43
  • ???jsp.display-item.citation.isi??? 39
social impact