Tetrazole compounds. 9 . A new approach to tetrazolyl‐substituted quinoline derivatives

The acid‐catalyzed reaction of 1‐aryl‐5‐(2‐dimethylaminovinyl)‐1 H ‐tetrazoles 2 with arylamines suitably functionalized in the ortho ‐position resulted in Z ‐configurated transamination products which were cyclized to novel 3‐tetrazolylquinolines by the action of sodium ethoxide. Thus, on reacting 2 with 2‐aminoacetophenone or 2‐aminobenzophenone, respectively, the 2‐[2‐(1‐aryl‐1 H ‐tetrazol‐5‐yl)vinyl‐amino]aryl ketones 3a‐g were obtained, the cyclization of which gave 4‐substituted 3‐(1‐aryl‐1 H ‐tetrazol‐5‐yl)quinolines 4 . In the case of the transamination products 3h‐1 , prepared from 2 and methyl anthranilate, the ring closure afforded 3‐(1‐aryl‐1 H ‐tetrazol‐5‐yl)‐1 H ‐quinolin‐4‐ones 5 . Starting from 2 and anthranilonitrile 4‐amino‐3‐(1‐aryl‐1 H ‐tetrazol‐5‐yl)quinolines 10 were obtained via the corresponding intermediates 9 .