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

Silvestre Buscemi; Andrea Pace; Ivana Pibiri; Nicolò Vivona; Domenico Spinelli

doi:10.1021/jo0262762

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

J Org Chem. 2003 Jan 24;68(2):605-8. doi: 10.1021/jo0262762.

Authors

Silvestre Buscemi¹, Andrea Pace, Ivana Pibiri, Nicolò Vivona, Domenico Spinelli

Affiliation

¹ Dipartimento di Chimica Organica A. Mangini, Università degli Studi di Bologna, Via S. Donato 15, Italy.

PMID: 12530892
DOI: 10.1021/jo0262762

Abstract

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.