Application of heterocyclic aldehydes as components in Ugi-Smiles couplings.
Efficient one-pot Ugi-Smiles couplings are reported for the use of furyl-substituted aldehyde components. In the presence of these heterocyclic aldehydes, reactions tolerated variations in amine components and led to either isolatedN-arylamide Ugi-Smiles adducts orN-arylepoxyisoindolines, products of tandem Ugi-Smiles Diels-Alder cyclizations, in moderate yields. A thienyl-substituted aldehyde was also a competent component for Ugi-Smiles adduct formation.
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
Katelynn M
KM
Mason
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
Michael S
MS
Meyers
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
Abbie M
AM
Fox
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, Illinois 62026, USA.
Sarah B
SB
Luesse
Diels–Alder cycloaddition; Ugi–Smiles coupling; epoxyisoindoline; multicomponent coupling reaction; tandem reaction