Solid-phase synthesis of 3-hydroxy-6-nitroquinolin-4(1H)-ones with two diversity positions.
The efficient solid-phase synthesis of 3-hydroxy-2,7-disubstituted-6-nitroquinolin-4(1H)-ones using Rink amide resin is described. Synthesis starts from immobilized 4-chloro-5-nitroanthranilic acid which, after the nucleophilic replacement of the chlorine atom with various amines and subsequent esterification with bromoacetophenones, afforded substituted phenacylanthranilates. Their cyclization by heating in sulfuric acid gave corresponding hydroxyquinolinones of excellent purity.
Department of Organic Chemistry, Faculty of Science, University of Palacky, 771 46 Olomouc, Czech Republic.
Sona
S
Krupková
Miroslav
M
Soural
Jan
J
Hlavác
Pavel
P
Hradil
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D006912:Hydroxyquinolines