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■ Preparation of New 3-Hydroxyquinoline Alkaloid, Jineol and Its Ether Derivatives Using Directed ortho-Lithiation of Chloroquinoline as the Key Step

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

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

A new alkaloid, jineol (3,8-dihydroxyquinoline) was conveniently prepared employing directed ortho-lithiation of chloroquinoline for 3-position of quinoline ring. Moreover, the ether derivatives of jineol were obtained by the reaction of jineol with alkyl halide in the presence of KOH in DMSO in 26-96% yields.