title: Multicomponent synthesis of substituted and fused-ring imidazoles via phospha-münchnone cycloaddition.
abstract: A new, one-pot synthesis of imidazoles from imines, acid chlorides, and N-nosyl imines or tethered nitriles is reported. The reaction is mediated by the phosphonite PPh(catechyl) and proceeds via regioselective cycloaddition with an in situ-generated phospha-münchnone 1,3-dipole. This provides an efficient route to construct both highly substituted and polycyclic imidazoles directly from available substrates, without metal catalysts, and with access to product diversity.
authors: Department of Chemistry, McGill University , 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada.
authors: Sara
authors: S
authors: Aly
authors: Mikhail
authors: M
authors: Romashko
authors: Bruce A
authors: BA
authors: Arndtsen
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles; D010165:Palladium
chemical_list: D007093:Imidazoles; D007097:Imines; D010080:Oxazoles; D010165:Palladium