New synthetic pathway to diverse 2-substituted quinolines based on a multicomponent reaction: solution-phase and solid-phase applications.
Using Kobayashi's modification of the Grieco reaction, we were able to synthesize diverse 4-phenylthio-1,2,3,4-tetrahydroquinolines. These intermediates were oxidized and subsequently pyrolized to provide the corresponding quinolines. This new approach to 2-substituted quinolines was exemplified by liquid-phase production of a 25-member library. This was extended to solid-phase chemistry, starting from (l)-4-nitrophenylalanine on Wang resin, for production of a 16-member library. The latter compounds possess potentially interesting VLA-4 antagonist properties.
Demaude
Thierry
T
Combinatorial Chemistry and Automation Group, Chemical Research, UCB Pharma S.A., Chemin du Foriest, 1420 Braine l'Alleud, Belgium.
Knerr
Laurent
L
Pasau
Patrick
P