Synthesis of oxindoles via reductive CO2 fixation

被引：11

作者：

Amaya, Toru ^{[1
]}

Kurata, Izumi ^{[1
]}

Hirao, Toshikazu ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 08期

关键词：

PINACOL COUPLING REACTION; GROWTH-HORMONE SECRETAGOGUES; CARBON-DIOXIDE; ALIPHATIC-ALDEHYDES; ASYMMETRIC ADDITION; CATALYTIC-SYSTEM; AROMATIC KETONES; DIARYL KETONES; ZINC METAL; ACIDS;

D O I：

10.1039/c6qo00107f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：929 / 933

页数：5

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