Synthesis of 3-Arylideneindolin-2-ones from 2-Aminophenols by Ugi Four-Component Reaction and Heck Carbocyclization

被引：33

作者：

Dai, Wei-Min ^{[1
,2
]}

Shi, Jianyu ^{[1
]}

Wu, Jinlong ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Asymmetr Catalysis & Synth, Hangzhou 310027, Peoples R China

[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

SYNLETT | 2008年 / 17期

基金：

中国国家自然科学基金;

关键词：

2-aminophenol; aryl triflate; Heck reaction; 2-oxindole; Ugi four-component reaction;

D O I：

10.1055/s-0028-1083505

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aminophenols underwent the Ugi four-component reaction (U-4CR) with trans-cinnamic acids, aromatic aldehydes and isocyanides in MeOH (50 degrees C, 48 h) to give the linear alpha-[N-(2-hydroxyphenyl)-substituted amido] carboxamides in 54-80% yields. Treatment of the 2-hydroxyphenyl moiety in the U-4CR products with NaH and PhNTf2 afforded the corresponding aryl triflates (77-100%), which were subjected to the intramolecular Heck reaction (IMHR) catalyzed by 3-5 mol% Pd(OAc)(2)-BINAP (MeCN, 180 degrees C, 30-60 min) under microwave heating to furnish alpha-(3-arylidene-2-oxindol-1-yl) carboxamides in 52-77% yields.

引用

页码：2716 / 2720

页数：5

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