Iodine-promoted imino-Diels-Alder reaction of fluorinated imine with enol ether: synthesis of 2-perfluorophenyl tetrahydroquinoline derivatives |
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Authors: | Guifang Jin Jianwei Han Jianmin Zhang |
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Institution: | a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China b Department of Chemistry, Shanghai University, Shanghai 200444, China |
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Abstract: | Iodine was used to catalyze the hetero-Diels-Alder reaction of pentafluorobenzylidineaniline (C6F5CH NAr 1) with enol ethers to afford the corresponding tetrahydroquinolines derivatives as a mixture of cis/trans stereoisomers in moderate yields. These products could also be prepared by one-pot, three-component reaction of pentafluorophenylaldehyde, anilines, and enol ethers under the same reaction condition. Mild and neutral reaction conditions, facile experimental procedure, and low price of iodine should make this method attractive for practical synthesis of many fluorinated tetrahydroquinoline derivatives. |
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Keywords: | Hetero-Diels-Alder reaction Imine Iodine catalyst Fluorinated tetrahydroquinoline Synthesis |
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