含窒素複素環化合物の合成研究(第37報)2-Phenylquinoline 1-Oxide類およびPhenyl-1,8-naphthyridine類の合成とその抗菌性について

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Reaction of quinoline 1-oxide (I) with o-, m-, or p-methoxyphenylmagnesium bromide in tetrahydrofuran afforded the corresponding 2-(o- or p-methoxyphenyl) quinoline 1-oxides (II and V) and their deoxygenated compounds, 2-(o-, m-, or p-methoxyphenyl) quinolines (III, IV, and VI). II, III, V, and VI were hydrolyzed with hydrobromic acid in acetic acid to form their hydroxy compounds (VII to X). Reaction of 1,8-naphtyridine 1-oxide (XI) with o-methoxyphenyllithium in ether afforded 2-(o-methoxyphenyl)-1,8-naphthyridine (XII) which was hydrolyzed to the hydroxy compound (XIII). Optimal conditions for the reaction of pyridine 1-oxide (XIV) and benzyne were examined and the best condition was applied to XI. Reaction by method b afforded 2- and 3-(o-hydroxyphenyl)-1,8-naphthyridines (XIII' and XIX). Antibacterial tests of the synthesized compounds and 2-phenyl-1,x-naphthyridine x=5,6,7,8) (XX to XXIII) showed that III had a wide antibacterial spectrum and that VIII had a stronger antibacterial activity than other compounds against Pseudomonas aeruginosa.
公益社団法人日本薬学会の論文
1979-05-25