Beilstein J. Org. Chem.2016,12, 2032–2037, doi:10.3762/bjoc.12.191
also a competent component for Ugi–Smiles adduct formation.
Keywords: Diels–Alder cycloaddition; epoxyisoindoline; multicomponent coupling reaction; tandem reaction; Ugi–Smiles coupling; Introduction
Synthetic methods to efficiently prepare libraries of biologically-relevant compounds are in demand
standard Ugi–Smiles adducts 3 (Table 3). The lack of oxatricyclic epoxyisoindoline formation is not surprising, given the more remote relative proximity of the diene and dienophile. Propargylamine and 3-butenylamine were also satisfying partners with 3-furaldehyde in this process.
Ugi–Smiles reactions with
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Graphical Abstract
Scheme 1: N-Arylepoxyisoindolines via tandem Ugi–Smiles/IMDA reaction.