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Multicomponent Reaction of Imidazo[1,5-a]pyridine Carbenes with Aldehydes and Dimethyl Acetylenedicarboxylate or Allenoates: A Straightforward Approach to Fully Substituted Furans

  作者 PAN HUANRUI; LI YONGJIA; YAN CAIXIA; XING JUAN; CHENG YING  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-19;  页码  6644-6652  
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[摘要]The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields. This work not only provided the first example of the application of imidazo[1,5-a]pyridin-3-ylidenes in organic synthesis but also developed a straightforward approach to fully substituted furans that are not easily accessible by other methods.

 
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