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Communication | Regular issue | Vol 14, No. 2, 1980, pp.179-184
Published online, 1st January, 1970
DOI: 10.3987/R-1980-02-0179
The Reaction of 4-Methoxyquinoline 1-Oxide with Dimethyl Acetylenedicarboxylate

Yasuhisa Ishigura, Kazuhisa Funakoshi, Seitaro Saeki, Masatomo Hamana,* and Ikuhiko Ueda

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

4-Methoxyquinoline 1-oxide reacts with dimethyl acetylenedicarboxylate in boiling dioxane affords N-quinolinium ethylide (1), 2-substituted quinoline (2), furo[3,2-c]quinoline (3) and 9-oxo-tetrahydro-cis-furo[3,2-b]quinoline (4). Similar reactions readily proceed at low temperatures in dichloromethane, acetonitrile and DMF to give 2, 3 and 4.