1973 年 93 巻 8 号 p. 1024-1033
Reaction of 5-nitroquinoline (I) with hydroxylamine was examined and the following reaction mechanism was presumed. In X, the ring hydrogen at the position to which hydroxylamine has added, makes a proton shift to both the nitrogen in the hydroxylamino group and oxygen in the nitro group, and two kinds of reaction progresses. The former reaction route (path a) produces 6-amino derivative (III) and the latter route (path b) gives furazano[3, 4-f]quinoline (VIII). The N-O bond in hydroxylamine is cleaved by the reaction of path a but remains in the molecule by the reaction of path b. In contrast, the N-O bond in hydroxylamine-O-sulfonic acid tends to be severed by the effect of the sulfo group and its reaction with I produces a large quantity of III, with only a minute amount of VIII. When the site of the reaction with reagents is conjugated with the ring-nitrogen in quinoline, formation of furazan compound is small.