Intramolecular Catalytic Friedel−Crafts Reactions with Allenyl Cations for the Synthesis of Quinolines and Their Analogues
journal contributionposted on 08.07.2004, 00:00 by Teruhiko Ishikawa, Shinobu Manabe, Toshiaki Aikawa, Takayuki Kudo, Seiki Saito
This paper describes a novel method to synthesize a quinoline backbone by incorporating allenyl cations into a catalytic intramolecular Friedel−Crafts reaction. The initial products were isomerized and aromatized upon treatment with acid and base, respectively, to give quinolines. The basic concept also proved to be promising for 1-benzazepine, 1-benzazocine, or isoquinoline synthesis.