6533b836fe1ef96bd12a0a3d
RESEARCH PRODUCT
On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the substituent effects in Boulton-Katritzky reactions
Franco GhelfiDomenico SpinelliVincenzo FrennaAntonio Palumbo-piccionellosubject
ProtonArylOrganic ChemistryMononuclear rearrangement of heterocycles substituent effect phenylisoxazolesSubstituentSettore CHIM/06 - Chimica OrganicaAtmospheric temperature rangePhenacylKinetic energyBiochemistryMedicinal chemistrychemistry.chemical_compoundchemistryDrug DiscoveryOrganic chemistryIsoxazoleBoulton-Katritzky reactions Isoxazoles Triazoles Ring-into-ring conversion Effect of substituents Free energy relationshipsdescription
Abstract The rearrangement of eight new Z -arylhydrazones of 3-benzoyl-5-phenylisoxazoles ( 3d – k ) into the relevant 2-aryl-4-phenacyl-2 H -1,2,3-triazoles ( 4d – k ) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a – c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-09-01 |