Reaction of N-Aminopyridinium Derivatives. IV. Syntheses of N-Aminoquinolinium Salts and Their Reaction with Cyanide Ion

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N-Aminoquinolinium iodide (I) was treated with alkali in dimethylformamide to afford N-iminoquinoline dimer (II) which was further converted into N-acetimidoquinoline (III) by the reaction with acetic anhydride and successive alkaline treatment. The addition of hydroiodic acid or methyl iodide to III provided N-acetamidoquinolinium iodide (IV) or N-methylacetamidoquinolinium iodide (V) respectively. Reaction of I, IV, and V with cyanide ion was investigated. In water, I provided four products ; 4-cyanoquinoline, 2, 4-dicyanoquinoline (VI), 4-cyanoquinaldamide (VII) and 2-(4-cyano-2-quinolyl)-s-triazolo [1, 5-α] quinoline (VIII), but in methanol two products ; 4-cyanoquinoline and VII. V was also reacted in water to give a reaction intermediate, 1-methylacetamido-2-cyano-1, 2-dihydroquinoline (X VI) which was easily decomposed to 2-cyanoquinoline and N-methylacetamide quantitatively. But IV did not afford any products as above and was recovered as its ylide compound (III).