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

摘要

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.