6533b827fe1ef96bd12871ab

RESEARCH PRODUCT

Synthesis of fluorinated 1,2,4-oxadiazin-6-ones through ANRORC rearrangement of 1,2,4-oxadiazoles

Antonio Palumbo PiccionelloAndrea PaceNicolò VivonaSilvestre BuscemiGianluca Giorgi

subject

Nucleophilic additionOrganic ChemistrySettore CHIM/06 - Chimica OrganicaRing (chemistry)BiochemistryMedicinal chemistryTurn (biochemistry)chemistry.chemical_compoundHydroxylaminechemistryYield (chemistry)Drug DiscoveryElectrophileOrganic chemistryOxadiazoles Oxadiazinones ANRORC rearrangement Fluorinated heterocycles

description

Abstract The reaction of 3-ethoxycarbonyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydroxylamines has been investigated, evidencing the possibility of competitive reaction paths. Nucleophilic addition of hydroxylamine to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring-opening and ring-closure with enlargement, leads to high yield and in very mild experimental conditions to the formation of 5-hydroxyamino-3-perfluoroalkyl-6 H -1,2,4-oxadiazin-6-ones, one of these presenting water gelation ability. In turn, reactions with N -methylhydroxylamine lead the exclusive formation of 4-perfluoroacylamino-2-methyl-2 H -1,2,5-oxadiazol-3-ones through the well known Boulton–Katritzky rearrangement.

yearjournalcountryeditionlanguage
2009-04-01Tetrahedron Letters
https://doi.org/10.1016/j.tetlet.2009.01.071