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Paper | Regular issue | Vol 51, No. 10, 1999, pp.2385-2397
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8632
Reaction of Quinoline N-Oxides with Alkyl- and Aryllithiums in the Presence of Oxidant

Yoshinobu Tagawa, Manami Nomura, Hiroyuki Yamashita, Yoshinobu Goto,* and Masatomo Hamana

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

Abstract

Quinoline and some 4-substituted quinoline 1-oxides react with alkyl- and aryllithiums in the presence of an oxidant to afford 2-alkyl- and 2-arylquinoline 1-oxides in generally good yields. Among oxidants used, 9-fluorenone is most effective. On the other hand, quinaldine 1-oxide undergoes a base-induced electrophilic reaction with n-BuLi and 9-fluorenone to give 2-[(9-hydroxyfluoren-9-yl)methyl]quinoline 1-oxide.