Synthesis and spectral data of quinoline products obtained by reaction of <i>N</i>‐(4‐pyridinyliden)anilines and <i>N</i>‐benzylidenaniline with 2,2‐dimethoxypropane (kametani reaction)

Abstract

Abstract magnified image 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.