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Tetrazole compounds. 9 . A new approach to tetrazolyl‐substituted quinoline derivatives
Author(s) -
Fischer Gerhard W.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310642
Subject(s) - chemistry , tetrazole , transamination , aryl , sodium ethoxide , sodium azide , quinoline , medicinal chemistry , ring (chemistry) , stereochemistry , organic chemistry , alkyl , ethanol , enzyme
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 .