Cyclization and oxidation of o-bromophenylacetamides for the synthesis of oxindoles and isoindigoes |
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| Authors: | Liang Liu Lei Song Yujun Guo Dewen Min Tianchao Shi Wu Zhang |
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| Institution: | Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, People''s Republic of China |
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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 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. |
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| Keywords: | Condensation Cyclization Isoindigo Oxidation Oxindole |
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