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A Novel Approach to 2,2-Disubstituted 1,2-Dihydro-4-phenylquinolines

✍ Scribed by Harald Walter

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
527 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The reaction of 2‐(1‐phenylvinyl)aniline and 4‐chloro‐2‐(1‐phenylvinyl)aniline with acetophenone derivatives, 1‐(naphthalen‐1‐yl)ethanone and 1‐(furan‐2‐yl)ethanone in toluene at 110–115° with toluene‐4‐sulfonic acid as a catalyst leads in good‐to‐excellent yields to the 2,2‐disubstituted 1,2‐dihydro‐4‐phenyl‐quinolines 1–18 (Scheme 1, Table). The structure of the new racemic 1,2‐dihydroquinolines 1–18 is determined by NMR spectroscopy. A reaction mechanism proceeding via a 6π‐electrocyclic rearrangement of 2‐(1‐phenylvinyl)anils 19 as the key step is proposed for the formation of these compounds (Scheme 1). The scope and limitations of the novel methods are discussed (Scheme 2).

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