Abstract
Quaternary salts of 4-azidoquinoline and 4-azidoquinoline 1-oxide were synthesized and their reaction was examined. Their decomposition with alkali afforded 1-methyl-(or methoxy)-4 (1H)-quinolone. Treatment of 1-methoxy-4-azidoquinolinium methosulfate with sodium alkoxides resulted in a reaction at room temperature to form 4-alkoxyquinolines. These compounds reacted with compounds possessing an active methylene to form 1-methyl (or methoxy)-4-aminoquinolinium methosulfate, instead of undergoing triazole cyclization. Thermal decomposition in toluene or catalytic hydrogenation also furnished the same amino compound.
