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Synthesis of 3-arylideneindolin-2-ones from 2-aminophenols by Ugi four-component reaction and Heck carbocyclization.

  作者 Dai, Wei-Min;Shi, Jianyu;Wu, Jinlong;  
  选自 期刊  SYNLETT;  卷期  2008年-17;  页码  2716-2720  
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[摘要]with trans-cinnamic acids, arom. aldehydes and isocyanides in MeOH (50? 48 h) to give the linear a-[N-(2-hydroxyphenyl)-substituted amido] carboxamides, e.g., I, 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 intramol. Heck reaction (IMHR) catalyzed by 3-5 mol% Pd(OAc)2-BINAP (MeCN, 180? 30-60 min) under microwave heating to furnish a-(3-arylidene-2-oxindol-1-yl) carboxamides, e.g., II, in 52-77% yields.

 
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