Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

Teruhiko Ishikawa; Shinobu Manabe; Toshiaki Aikawa; Takayuki Kudoh; Seiki Saito

doi:10.1021/ol049301u

Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

Teruhiko Ishikawa, Shinobu Manabe, Toshiaki Aikawa, Takayuki Kudoh, Seiki Saito

Research output: Contribution to journal › Article › peer-review

67 Citations (Scopus)

Abstract

(Equation Presented) 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.

Original language	English
Pages (from-to)	2361-2364
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	14
DOIs	https://doi.org/10.1021/ol049301u
Publication status	Published - Jul 8 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Equation Presented) 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.",

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AU - Ishikawa, Teruhiko

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AU - Aikawa, Toshiaki

AU - Kudoh, Takayuki

AU - Saito, Seiki

PY - 2004/7/8

Y1 - 2004/7/8

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Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues

Abstract

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