Cyclization and oxidation of o-bromophenylacetamides for the synthesis of oxindoles and isoindigoes. Issue 2 (11th January 2018)

• Record Type: Journal Article
• Authors: Liu, Liang; Song, Lei; Guo, Yujun; Min, Dewen; Shi, Tianchao; Zhang, Wu
• Is Part Of: Tetrahedron. Volume 74:Issue 2(2018)
• Page Start: 354
• Page End: 359
• Publication Date: 2018-01-11
• Subjects: Condensation -- Cyclization -- Isoindigo -- Oxidation -- Oxindole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.12.005
• Languages: English
• ISSNs: 0040-4020

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. Graphical abstract: