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A Revisit to the Hantzsch Reaction: Unexpected Formation of Tetrahydrobenzo[b]pyrans beyond Polyhydroquinolines

  作者 UNDALE KEDAR A; PARK YOONKOOK; PARK KYUNGMOON; DAGADE DILIP H; PORE DATTAPRASAD M  
  选自 期刊  SYNLETT;  卷期  2011年-6;  页码  791-796  
  关联知识点  
 

[摘要]A competitive multicomponent synthesis of tetrahydrobenzo[b]pyrans over polyhydroquinolines is achieved in the presence of ammonium acetate at ambient temperature in ethanol medium. The formation of tetrahydrobenzo[b]pyran instead of polyhydroquinoline in solution phase has been confirmed by spectral and single-crystal analysis. The mechanism for the above transformation is suggested and supported by semi-empirical calculations of heat of formation for the intermediates as well as products.

 
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