A novel and efficient one-pot multi-component reaction of pentafluorobenzaldehyde, alkynes and anilines for the synthesis of 2-pentafluorophenyl substitutedquinolines under microwave irradiation and a solvent-free condition is presented.
Iodine was used to catalyze the hetero-Diels-Aider 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 onepot, 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. (C) 2009 Elsevier Ltd. All rights reserved.
Saeed, A. A. H.; El-Ashhab, F. S.; Muhammed, H. F., Egyptian Journal of Chemistry, 2002, vol. 45, # 3, p. 527 - 538
作者:Saeed, A. A. H.、El-Ashhab, F. S.、Muhammed, H. F.、Shicha, L. A.