ANTIMALARIALS .4. A NEW SYNTHESIS OF ALPHA-(2-PYRIDYL)- AND ALPHA-(2-PIPERIDYL)-2-ARYL-4-QUINOLINEMETHANOLS

New convenient syntheses of α-(2-pyridyl)- and α-(2-piperidyl)-2-aryl-4-quinolinemethanols are reported. The key steps involve addition of pyridyllithium to quinoline-4-carboxylic acids and subsequent one-step selective catalytic 8 H hydrogenation of the ketopyridyl system to the α-piperidylmethanol. All of the α-piperidylmethanols were highly active against Plasmodium berghei in mice but were phototoxic, whereas the α-pyridyl analogs were considerably less phototoxic but were inactive. © 1968, American Chemical Society. All rights reserved.