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A Versatile Synthesis of 3-Substituted 4-Cyano-1,2,3,4-tetrahydro-1-oxo-beta-carbolines

  作者 HUBER KILIAN; KAST OLIVER; BRACHER FRANZ  
  选自 期刊  Synthesis;  卷期  2010年-22;  页码  3849-3854  
  关联知识点  
 

[摘要]In a project aimed at the synthesis of analogues of the cytotoxic beta-carboline alkaloid bauerine C with more advantageous solubility properties, a 3-amino analogue was prepared by treating ethyl 3-(cyanomethyl)indole-2-carboxylate with ammonia. Upon addition of aldehydes or ketones to the reaction mixture, 3-substituted 4-cyano-1,2,3,4-tetrahydro-1-oxo-beta-carbolines were obtained in a one-pot condensation. When cyclic ketones are used, the procedure allows a convenient synthesis of tetracyclic spiro compounds.

 
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