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

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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
Lingua originaleEnglish
pagine (da-a)235-244
Numero di pagine10
Stato di pubblicazionePublished - 2009

All Science Journal Classification (ASJC) codes

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