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Synthesis of Thieno[2,3-b]quinolinone Derivatives

  作者 HAN GUANGFAN; WANG MING; CHEN LIZHUANG; HU XIAOLEI  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2012年49-4;  页码  909-912  
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[摘要]The Knoevenagel reactions of malononitrile with acetophenone or 4-substituted acetophenons were carried to give the corresponding 2-(1-aryle thylidene)malononitriles, which was further cyclized with sulfur using NaHCO3 as catalysts to generate 2-amino-5-arylthiophene-3-carbonitrile 2. The intermediate enamines 3 were prepared by refluxing of 2 with 5-substituted-1,3-cyclohexanedione using p-toluenesulfonic acid as catalyst. The title compounds 4-amino-3-aryl -7-substituted-7,8-dihydrothieno[2,3-b]quinolin-5(6H)-one were synthesized by cyclization of 3 in the presence of K2CO3 and Cu2Cl2. The structures of all compounds were characterized by elemental analysis, IR, MS, and 1H-NMR spectra.

 
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