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DOI: 10.1055/s-0030-1258229
Formation of 1,2-Dihydroquinoline-3-carboxylic Acid Derivatives from Methyl 3-(Arylamino)acrylates with Hydrogen Iodide
Publikationsverlauf
Publikationsdatum:
25. August 2010 (online)
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Abstract
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.
Key words
cyclization - hydrogen iodide - heterocycles - solvent effects - substituent effects
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References
MeO-5a can be converted to 5a in 86% yield by the reaction of MeO-5a with HI in MeCN.