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Communication | Special issue | Vol 7, No. 2, 1977, pp.801-806
Published online, 1st January, 1970
DOI: 10.3987/S-1977-02-0801
A Novel Formation of Cyclopropa[c]quinolines from Some 2-Substituted Quinoline N-Oxides

Seitaro Saeki, Haruyoshi Honda, Yoshio Kaku, Kazuhisa Funakoshi, and Masatomo Hamana*

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

Abstract

2-Chloroquinoline N-oxide (1) reacts with ethyl cyanoacetate in the presence of benzoyl chloride and triethylamine to give ethyl 1-cyano-2-oxo-1a,2,3,7b-tetrahydrocyclopropa[c]quinoline-1-carboxylate (2) in 78% yield. The reaction of 2-phenylquinoline N-oxide also affords ethyl 1-cyano-2-phenyl-1a,7b-dihydrocyclopropa[c]quinoline-1-carboxylate though in a lower yield. The reaction of 1 with malonodinitrile gives not a cyclopropaquinoline but 1-benzoyloxy-2-(α,β-dicyanomethylene)-1,2-dihydroquinoline.