6533b82dfe1ef96bd1291395
RESEARCH PRODUCT
A Photochemical One-Pot Three-Component Synthesis of Tetrasubstituted Imidazoles
Stefan PuschTill Opatzsubject
chemistry.chemical_compoundReaction mechanismchemistryComponent (thermodynamics)Organic ChemistryCondensationPhysical and Theoretical ChemistryIsoxazoleCleavage (embryo)Ring (chemistry)PhotochemistryBiochemistrydescription
Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, α-aminonitriles, and isoxazoles. Condensation of the first two components produces α-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C(2)-C(3) bond of the acylazirine. The reaction mechanism was studied by DFT calculations.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-10-07 | Organic Letters |