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.
Richey, Bree; Mason, Katelynn M.; Meyers, Michael S.; and Luesse, Sarah, "Rapid Access to Conformationally-Constrained Oxatricycles via Ugi-Smiles Couplings" (2016). SIUE Faculty Research, Scholarship, and Creative Activity. 47.