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

PALUMBO PICCIONELLO, A., Pace, A., Buscemi, S., Vivona, N. (2009). An ANRORC approach to the synthesis of perfluoroalkylated 1,2,4-triazole-carboxamides. ARKIVOC, 2009(vi), 235-244.

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

PALUMBO PICCIONELLO, Antonio;PACE, Andrea;BUSCEMI, Silvestre;VIVONA, Nicolo'
2009-01-01

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
2009
Settore CHIM/06 - Chimica Organica
PALUMBO PICCIONELLO, A., Pace, A., Buscemi, S., Vivona, N. (2009). An ANRORC approach to the synthesis of perfluoroalkylated 1,2,4-triazole-carboxamides. ARKIVOC, 2009(vi), 235-244.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/34825
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