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Abstract N-substituted oxindoles were obtained through a facile KOH/DMSO promoted intramolecular cyclization of o-bromophenylacetamides in good yields. Furthermore, isoindigo derivatives were readily synthesized through sequential intramolecular cyclization, oxidation and condensation… Click to show full abstract
Abstract N-substituted oxindoles were obtained through a facile KOH/DMSO promoted intramolecular cyclization of o-bromophenylacetamides in good yields. Furthermore, isoindigo derivatives were readily synthesized through sequential intramolecular cyclization, oxidation and condensation of o-bromophenylacetamide in the presence of copper (II) acetate monohydrate, iodobenzene diacetate and KOH/DMSO. This method provides a convenient synthesis of a range of oxindoles and symmetrical biologically important (E)-bisindole-2-ones using o-bromophenylacetamide as sole starting material. The reaction mechanism is elucidated in light of the control experiment results.
Journal Title: Tetrahedron
Year Published: 2018
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