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

  作者 HAN GUANGFAN; CUI BIN; CHEN LIZHUANG; JIN YAN  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2010年47-6;  页码  1335-1339  
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[摘要]A series of novel 11-amino-3,3-dimethyl-8-substituted-12-aryl-3,4,7,8,9,12-hexahydro-2H-be nzopyran[2.3-b]quinoline-1,10-dione derivatives 4 were synthesized by 2-amino-3-cyano-4-aryl-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-benzopyr an 2 with 5-substituted-1,3-cyclohexanedione using p-toluenesulfonic acid. K2CO3, and Cu2Cl2 as catalysts. The compounds 2 as easily accessible precursors were obtained from 5,5-dimethyl-1,3-cyclohexanedione by Michael addition with beta-dicyanostyrenes 1, prepared by Knoevenagel condensation of different aromatic aldehydes and malononitrile. The synthesis of the title compounds 4 completed by one-pot reaction of 4-aryl-4H-benzopyran derivatives with 5-substituted-1.3-cyclohexanediones by refluxing in toluene using TsOH as catalyst. The structures of all compounds were characterized by elemental analysis, IR, MS, and (HMR)-H-1 spectra.

 
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