Zinc Lewis acid-catalyzed cyclization of ethenetricarboxylate derivatives 1 with 2-ethynylanilines has been examined. Reaction of 1,1-diethyl 2-tert-butyl ethenetricarboxylate 1b with 2-(trimethylsilylethynyl)aniline substrates in the presence of Zn(OTf)(2) gave bridged quinoline derivatives in 43-85% yield. The reaction of 1b with 2'-aminoacetophenone also gave the bridged quinoline derivative in 41% yield. Thermal reaction of bridged quinolines (180-190 degrees C) afforded indole derivatives in moderate to good yields.
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