Synthesis of oxindoles via reductive CO2 fixation‡
Literature Information
Publication Date
2016-06-29
DOI
10.1039/C6QO00107F
Impact Factor
5.281
Authors
Toru Amaya, Izumi Kurata
View Original
Abstract
The synthesis of 3-aryl-3-hydroxy-2-oxindoles, which are a structural motif found in various natural products and pharmaceutically active compounds, was conducted via reductive coupling of (2-aminophenyl)(aryl)methanone derivatives and CO2 as a key step. The conditions employing Mg with chlorotrimethylsilane in DMA are the best for the reductive coupling, where the aryl halide moiety is intact. This reaction proceeds well without the protection of the amino group. The reductive coupling and acid-catalyzed lactam formation can be performed in a one-pot reaction to give the oxindoles.
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Organic Chemistry Frontiers
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