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Formation of 1,2-Dihydroquinoline-3-carboxylic Acid Derivatives from Methyl 3-(Arylamino)acrylates with Hydrogen Iodide

  作者 MATSUMOTO SHOJI; MORI TAKAHIRO; AKAZOME MOTOHIRO  
  选自 期刊  Synthesis;  卷期  2010年-21;  页码  3615-3622  
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[摘要]The reaction of methyl 3-(arylamino)acrylates with hydrogen iodide gave 1,2-dihydroquinoline-3-carboxylic acid derivatives at room temperature. This reaction proceeds efficiently in alcoholic solvent; bulky tert-butyl alcohol is the best solvent to give the 1,2-dihydroquinoline derivatives. It is particularly interesting that hydrogen iodide is the most efficient acid to achieve this reaction in tert-butyl alcohol. Various substituents at the phenyl ring are applicable. Compounds bearing meta-substituted phenyl ring with electron-donating group led to the corresponding 1,2-dihydroquinoline derivatives in good yields.

 
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