TY - JOUR
T1 - An ANRORC approach to the synthesis of perfluoroalkylated 1,2,4-triazole-carboxamides
AU - Buscemi, Silvestre
AU - Pace, Andrea
AU - Vivona, Nicolo'
AU - Palumbo Piccionello, Antonio
PY - 2009
Y1 - 2009
N2 - A series of perfluoroalkyl-1,2,4-triazole-carboxamides has been obtained through an ANRORClikerearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5-perfluoroalkyl-1,2,4-oxadiazole-3-carboxamides with methylhydrazine or hydrazine. The initialaddition 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 undermild experimental conditions. In some cases, a competitive ANRORC-enlargement reaction toform 1,2,4-triazin-6-ones was also observed. Obtained carboxamidotriazoles have also beenexplored as precursors for the synthesis of 3(5)-perfluoroalkyl-1,2,4-triazoles
AB - A series of perfluoroalkyl-1,2,4-triazole-carboxamides has been obtained through an ANRORClikerearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5-perfluoroalkyl-1,2,4-oxadiazole-3-carboxamides with methylhydrazine or hydrazine. The initialaddition 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 undermild experimental conditions. In some cases, a competitive ANRORC-enlargement reaction toform 1,2,4-triazin-6-ones was also observed. Obtained carboxamidotriazoles have also beenexplored as precursors for the synthesis of 3(5)-perfluoroalkyl-1,2,4-triazoles
KW - ANRORC rearrangements
KW - Fluorinated heterocycles
KW - oxadiazole
KW - triazole
KW - ANRORC rearrangements
KW - Fluorinated heterocycles
KW - oxadiazole
KW - triazole
UR - http://hdl.handle.net/10447/34825
M3 - Article
VL - 2009
SP - 235
EP - 244
JO - Arkivoc
JF - Arkivoc
SN - 1551-7004
ER -