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Communication | Regular issue | Vol 34, No. 12, 1992, pp.2243-2246
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6145
Electrophilic Reaction of Quinoline 1-Oxide through Base-induced Deprotonation

Yoshinobu Tagawa, Kazuya Hama, Yoshinobu Goto,* and Masatomo Hamana

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka, 814-01, Japan

Abstract

Lithiation of quinoline 1-oxide-BF3 complex (3) with LTMP and TMEDA in ether at -78 °C followed by treatement with benzaldehyde or cyclohexanone affords the corresponding 2-substituted derivatives (4, 5 or 6), while the reaction of quinoline 1-oxide (1) itself under the same conditions results in the formation of 2,2’-biquinoline 1-oxide (2).