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A Facile Method for the Synthesis of 3-Substituted 3-(Alkylthio)oxindoles or 3-Alkoxyoxindoles

  作者 ZHU FENG; ZHOU FENG; CAO ZHONGYAN; WANG CHAO; ZHANG YONGXUE; WANG CUIHONG; ZHOU JIAN  
  选自 期刊  Synthesis;  卷期  2012年44-20;  页码  3129-3144  
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[摘要]We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio) ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio) or 3-alkoxy-3-allyloxindoles.

 
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