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An Efficient, One-Pot Regioselective Synthesis of Highly Functionalized Chromen-5-ones and Pyrano[3,2-c]chromen-5-ones via a Tandem Knoevenagel-Michael-Cyclization Sequence

  作者 KAMALRAJA JAYABAL; MURALIDHARAN DORAISWAMY; PERUMAL PARAMASIVAN THIRUMALAI  
  选自 期刊  SYNLETT;  卷期  2012年-20;  页码  2894-2898  
  关联知识点  
 

[摘要]A facile, convenient, efficient, and high-yielding regioselective synthesis of a combinatorial library of hitherto unreported highly functionalized chromen-5-ones and pyrano[3,2-c]chromen-5-ones has been developed by one-pot three-component coupling of substituted aromatic aldehydes, dimedone/4-hydroxycoumarin with NMSM in the presence of catalytic amount of piperidine in ethanol medium. This transformation presumably proceeds via domino Knoevenagel condensation-Michael addition-intermolecular cyclization sequence creating three new bonds (two C-C and one C-O) and one stereocenter in a single operation.

 
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