6533b870fe1ef96bd12cfc91
RESEARCH PRODUCT
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
Andrea PaceSilvestre BuscemiIvana PibiriNicolò VivonaDomenico Spinellisubject
chemistry.chemical_classificationNucleophilic additionDouble bondOrganic ChemistryHydrazineOxadiazoleGeneral MedicineRing (chemistry)Medicinal chemistryChemical synthesischemistry.chemical_compoundchemistryReagentTriazole derivativesOrganic chemistryMoietydescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-06-03 | The Journal of Organic Chemistry |