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Communication | Regular issue | Vol 4, No. 3, 1976, pp.453-459
Published online, 1st January, 1970
DOI: 10.3987/R-1976-03-0453
Reaction of 3-Bromo-4-nitroquinoline 1-Oxide with Enamines. A Novel Cyclization Reaction to Furo[3,2-b]quinoline System

Hiroshi Noda, Teruo Yamamori, Mitsutaka Yoshida, and Masatomo Hamana*

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


3-Bromo-4-nitroquinoline 1-oxide (1) reacts with 1-morpholinocyclohexene at room temperature in chloroform to give 10-nitrotetrahydrobenzofuro[3,2-b]quinoline (2) in high yield via the primary adduct of the 1,3-dipolar cycloaddition reaction. The scope of this type of reaction is widespread, but similar reactions of 3-bromo- and 3-bromo-4-methoxyquinoline 1-oxides afford 2-(2-oxocyclohexyl)-3-morpholinoquinoline (14a) and its 4-methoxy derivative (14b).