General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C–H acids in aprotic media promoted by combination of strong bases and silylating agents

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• 作者：Micha? Wi?c?aw ; Mariusz Bobin ; Andrzej Kwast ; Robert Bujok…
• 关键词：Carbanions ; Heterocycles ; Nucleophilic substitution ; Aromatic substitution ; Nucleophilic addition ; Elimination ; Cyanides ; Nitroarenes
• 刊名：Molecular Diversity
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：19
• 期：4
• 页码：807-816
• 全文大小：679 KB
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• 作者单位：Micha? Wi?c?aw (1)
  Mariusz Bobin (1)
  Andrzej Kwast (1)
  Robert Bujok (1)
  Zbigniew Wróbel (1)
  Krzysztof Wojciechowski (1)
  
  1. Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Analytical Chemistry
  Polymer Sciences
  Organic Chemistry
  Pharmacy
  
• 出版者：Springer Netherlands
• ISSN：1573-501X

文摘

Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form \(\sigma ^\mathrm{H}\)-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields. Keywords Carbanions Heterocycles Nucleophilic substitution Aromatic substitution Nucleophilic addition Elimination Cyanides Nitroarenes