1. Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. Tel.: +27‐12‐429‐8805;2. Fax: +27‐12‐429‐8549
Abstract:
Staudinger reaction of the 2‐aryl‐4‐azido‐3‐bromoquinolines and 2‐aryl‐4‐azido‐3‐iodoquinolines with triphenyl phosphine in refluxing tetrahydrofuran afforded series of 2‐aryl‐3‐halogeno‐4‐(triphenylphosphoranylideneamino)quinolines. The latter were, in turn, hydrolyzed to the corresponding primary 4‐amino‐2‐aryl‐3‐(bromo/iodo)quinolines using 80% acetic acid under reflux. Tetrakis(triphenylphosphine)‐palladium(O)‐catalyzed Suzuki reaction of the 2‐aryl‐3‐iodo‐4‐(triphenylphosphoranylideneamino)‐quinolines with phenylboronic acid in dimethyl formamide in the presence of 2 M K2CO3 followed by hydrolysis of the incipient 2,3‐diaryl‐4‐(triphenylphosphoranylideneamino)quinolines with 80% acetic acid afforded the 4‐amino‐2,3‐diarylquinolines.
