6533b7d3fe1ef96bd12613f0
RESEARCH PRODUCT
Synthesis of trifluoromethylated 2-benzoyl- and 2-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivatives
Silvestre BuscemiMarcella PaniAntonio Palumbo PiccionelloNicolò VivonaAndrea Pacesubject
chemistry.chemical_compoundHydrolysisMontmorillonitechemistryOrganic ChemistryDrug DiscoveryCondensationMoietyOxadiazoleRing (chemistry)BiochemistryMedicinal chemistrydescription
Abstract Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated β-dicarbonyl compounds and subsequent base-induced Boulton–Katritzky Rearrangement (BKR) of the isolated β-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-04-01 |