6533b853fe1ef96bd12ac14e
RESEARCH PRODUCT
Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements
Annamaria MartoranaSilvestre BuscemiAntonio Palumbo-piccionelloGianluca GiorgiAndrea Pacesubject
Molecular StructureStereochemistryAcylationOrganic ChemistryImidazolesSequence (biology)Settore CHIM/06 - Chimica OrganicaIsoxazolesPhenacylBiochemistryHeterocyclic rearrangement isoxazole imidazole tandem reactions.Acylationchemistry.chemical_compoundReaction sequencechemistrySide chainImidazoleMoleculeIminesPhysical and Theoretical ChemistryIsoxazoleOxidation-Reductiondescription
A novel base-induced rearrangement of isoxazoles into imidazole derivatives is reported. In the isoxazole series, this represents the first example of a three-atom side-chain rearrangement involving a CNC sequence. The reactions are carried out under nitrogen and produced 2-aryl-4(5)-phenacyl-5(4)-phenyl-imidazoles in high yields. In the presence of oxygen, a cascade rearrangement-oxidation reaction sequence was observed and imidazole derivatives bearing an oxidized side-chain were isolated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-11-12 | Org. Biomol. Chem. |