2-Substituted-Isoindoles: A Novel Synthetic Route and a Study of the Diels–Alder and Michael Reactions

A novel one-step procedure for the synthesis of 2-substituted-isoindoles and 1-aryl-2-substituted-isoindoles is described. The procedure is based on the reaction of 2-(bromomethyl)benzaldehyde or 2-(bromomethyl)benzophenone derivatives with primary aromatic or aliphatic amines. Reactions of 1,2-diarylisoindoles with N-phenylmaleimide were studied. Refluxing the reactants in i-PrOH in the presence of triethylamine leads to the formation of Diels-Alder endo-adducts; whilst refluxing in AcOH in the presence of AcONa affords Michael adducts. The structure of the latter was confirmed by X-ray diffraction.