Intramolecular catalytic friedel-crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

T Ishikawa, S Manabe, T Aikawa, T Kudo, S Saito

Index: Ishikawa, Teruhiko; Manabe, Shinobu; Aikawa, Toshiaki; Kudo, Takayuki; Saito, Seiki Organic Letters, 2004 , vol. 6, # 14 p. 2361 - 2364

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Citation Number: 51

Abstract

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.