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Paper | Regular issue | Vol 55, No. 9, 2001, pp.1771-1777
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9295
Reaction of Quinoline 1-Oxides with Sodium Methoxide in the Presence of Lead(IV) Acetate

Yoshinobu Tagawa,* Keitaro Tanaka, Katsuya Yamashita, Yoshinobu Goto, and Masatomo Hamana

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nakamura, Jonan-ku, Fukuoka, 814-0180, Japan


In the presence of lead(IV) acetate, the reaction of quinoline 1-oxide with methoxide anion under various reaction conditions gives 2-methoxyquinoline 1-oxide without deoxygenation of N-oxide group. Reaction of 4-substituted quinoline 1-oxides with methoxide anion also resulted in the corresponding 4-substituted 2-methoxyquinoline 1-oxides under the same reaction conditions. As the reaction mechanism, ionic pathway is suggested rather than radical pathway through the investigation using radical initiators.