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Communication | Special issue | Vol 30, No. 2, 1990, pp.779-782
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S100
Reinvestigation of the Reaction of 3-Bromo-4-nitroquinoline 1-Oxide with 1-Morpholinocyclohexene

Yutaka Miura, Yasuo Fujimura, Sakae Takaku, and Masatomo Hamana*

*Chugai Pharmaceutical Company, Ltd., 135, 1-Chome Komakado, Gotemba City, shizuoka 412-8513, Japan


Reinvestigation of the reaction of 3-bromo-4-nitroquinoline-1-oxide (2) with 1-morpholinocyclohexene (3) has revealed that the reaction proceeds by a multistep ionic process involving the initial formation of 3-morpholino-4-nitro-2-(2-oxocyclohexyl)quinoline (6) and the subsequent tranformation of 6 into 10-nitro-1,2,3,4-tetrahydrobenzofuro[3,2-b]quinoline (5). Not only 2 reacts with various enamines in the same way, but also 3-bromo-4-nitropyridine N-oxide (7) undergoes the same type of reactions.