✦ LIBER ✦

Synthesis and spectral data of quinoline products obtained by reaction of N-(4-pyridinyliden)anilines and N-benzylidenaniline with 2,2-dimethoxypropane (kametani reaction)

✍ Scribed by Vladimir V. Kouznetsov; Carlos M. Meléndez Gómez; Juan M. Urbina González; Elena E. Stashenko; Ali Bahsas; Juan Amaro-Luis

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 142 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440308

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✦ Synopsis

Abstract

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A study on interaction between N‐(4‐pyridinyliden)anilines 1‐4 and 2,2‐dimethoxypropane under Kametani reaction conditions was realized. According to the GC‐MS analysis of crude reaction, besides the needed 4‐methyl‐2‐(4‐pyridinyl)quinolines 5‐8, three collateral products: secondary amines 9‐12, 4‐(2‐methylprop‐1‐enyl)quinolines 13‐16 and 4‐(2‐methoxy‐2‐methylpropyl)quinolines 17‐20 were formed. Unexpected quinolines 13‐16 as well the desired quinolines 5‐8 were isolated and fully characterized. In contrast, a condensation of N‐benzylidenaniline 21 with 2,2‐dimethoxypropane afforded a set of different quinoline products.

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