Practical and simple synthesis of substituted quinolines by an HCl-DMSO system on a large scale: remarkable effect of the chloride ion.
[reaction: see text] A variety of substituted quinolines are synthesized from imines and enolizable carbonyl compounds under aerobic conditions, in which only water is a byproduct. In DMSO, a catalytic amount of HCl activates carbonyl compounds quite effectively to give the quinolines. A simple and practical procedure is demonstrated on a large scale.
Tanaka
Shin-Ya
SY
Department of Applied Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Yasuda
Makoto
M
Baba
Akio
A
D002712:Chlorides; D004121:Dimethyl Sulfoxide; D006851:Hydrochloric Acid; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
D002712:Chlorides; D007202:Indicators and Reagents; D011804:Quinolines; D006851:Hydrochloric Acid; D004121:Dimethyl Sulfoxide