Direct α-amination of nitrones achieved by DBU-activated N-haloimides

Abstract Direct α-amination of nitrones has been developed by using N -haloimide-DBU protocol. Reaction of nitrones with N -haloimide takes place readily in the presence of DBU in DCM, affording directly α-aminonitrones in moderate to excellent yields. N -Haloimide activated by DBU provides both a halogen cation and a nitrogen anion source. E - and Z -isomerization of α-aminonitrones was examined and found to be highly sensitive to acidic substances like silica gel and Bronsted acid. In addition to nitrones, quinoline N -oxides are also suitable substrates. Direct amination achieved by the protocol demonstrates new reactivity of nitrones and quinoline N -oxides.