1983 Volume 103 Issue 6 Pages 601-606
Reaction of 6-nitroquinoline (1) with potassium cyanide in methanol was analyzed. The major products were 5-cyano-6-methoxyquinoline (2) and 1-aminoisoxazolo[4, 3-f]-quinoline (3). An acidic product, 4-oxo-3, 4-dihydro-1, 2, 3-triazino[4, 5-f]quinoline (8) was isolated. The structure of 8 was confirmed by synthesis from 6-aminoquinoline-5-carboxamide. Compound 8 was confirmed by synthesis from 6-aminoquinoline-5-carboxamide. Compound 8 could be prepared from 3 and hydroxylamine in alkaline solution : this suggested that NO- was eliminated from the primary intermediate, 5-cyano-6-nitrosoquinoline, by nucleophilic attack of methoxide anion perticipates. This also explains the formation of the major product, 2. The formation of the isoxazole derivative (3) is interpreted by the nucleophilic perticipation of cyanide anion. The mechanism proposed satisfies the observation obtained by isotope experiments.
