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Paper | Regular issue | Vol 31, No. 7, 1990, pp.1325-1331
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5413
Deoxygenative 2-Alkoxylation of Quinoline 1-Oxide

Mitsuo Hayashida, Haruyoshi Honda, and Masatomo Hamana*

*Faculty of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka 812, Japan

Abstract

Treatment of quinoline 1-oxide (1) with ethyl chloroformate or tosyl chloride and triethylamine in some lower alcohols affords the corresponding 2-alkoxyquinolines (2a-f) in generally satisfactory yields. Reactions of 2-methylpyridine and 2-methylquinoline 1-oxides lead to the corresponding 2-ethoxycarbonyloxymethyl (3 and 5) and 2-ethoxymethyl derivatives (4 and 6).