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Convenient MCRs Synthesis of Trifluoromethylated Pyrano[4,3-b]pyrans and Their Further Transformation

  作者 WANG WEI; LI JIA; ZHANG LI; SONG LIPING; ZHANG MIN; CAO WEIGUO; DENG HONGMEI; SHAO MIN  
  选自 期刊  Synthesis;  卷期  2012年44-11;  页码  1686-1692  
  关联知识点  
 

[摘要]Ethyl 2-hydroxy-7-methyl-5-oxo-4-aryl-2-(trifluoromethyl)-3,4-dihydro-2H, 5H-pyrano[4,3-b]pyran-3-carboxylate derivatives were synthesized via a one-pot three-component reaction (MCR) promoted by ammonium acetate. The effect of ammonium acetate and the solvent on the reaction efficiency was investigated. Furthermore, treatment of the resultant products with thionyl chloride/pyridine in chloroform gave the corresponding dehydrated products ethyl 4-aryl-7-methyl-5-oxo-2-(trifluoromethyl)-4H,5H-pyrano[4,3-b]pyran-3-carboxylates and the unexpected defluorinated products ethyl 3-aryl-6-methyl-4-oxo-4H-furo[3,2-c]pyran-2-carboxylates. The novel products are highly important for the synthesis of related fluorinated fused heterocyclic compounds.

 
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