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Synthesis of Imidazo[1,2-a]pyridines by the Bis(acetyloxy)(phenyl)-lambda(3)-iodane-Mediated Oxidative Coupling of 2-Aminopyridines with beta-Keto Esters and 1,3-Diones

  作者 WANG XIANPEI; MA LIJUAN; YU WEI  
  选自 期刊  Synthesis;  卷期  2011年-15;  页码  2445-2453  
  关联知识点  
 

[摘要]Imidazo[1,2-a]pyridine-3-carboxylates can be prepared directly from 2-aminopyridines and beta-keto esters by using bis(acetyloxy)(phenyl)-lambda(3)-iodane as an oxidant and boron trifluoride etherate as a catalyst. The amount of catalyst plays a key role in determining the course of the reaction. Whereas the use of 0.2 equivalents of catalyst ensures the generation of imidazo[1,2-a]pyridines, raising the amount of catalyst to 1.0 equivalents results in exclusive alpha-acetoxylation of the beta-keto esters. 2-Aminopyridines can also react with 1,3-diones to afford 3-acylimidazo[1,2-a]pyridines.

 
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