Use of allylamine and substituted 2-furaldehydes as components in Ugi–Smiles couplings of 2-nitrophenol provide ready access to N-aryl epoxyisoindolines. These adducts form via a dual event involving the Ugi–Smiles multicomponent reaction and an intramolecular Diels–Alder cycloaddition with the furan ring.