Fluorinated heterocyclic compounds. An expedient route to 5-perfluoroalkyl-1,2,4-triazoles via an unusual hydrazinolysis of 5-perfluoroalkyl-1,2,4-oxadiazoles: first examples of an ANRORC-like reaction in 1,2,4-oxadiazole derivatives.
The hydrazinolysis reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ring-closure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.
Buscemi
Silvestre
S
Dipartimento di Chimica Organica A. Mangini, Università degli Studi di Bologna, Via S. Donato 15, Italy.
Pace
Andrea
A
Pibiri
Ivana
I
Vivona
Nicolò
N
Spinelli
Domenico
D