Syntheses of Nitrogen-containing Heterocyclic Compounds. XXIII. Reaction of Naphthyridine Derivatives, with Special Reference to that of 1,7-Naphthyridine

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1,7-Naphthyridine (II) was prepared by the reduction of 8-chloro-1,7-naphthyridine over palladium-carbon. 1,5-Naphthyridine 1-oxide (III) and 1,5-naphthyridine (IV) were synthesized by the reaction of 3-aminopyridine 1-oxide with glycerol in the presence of Sulfo-mix, ferrous sulfate, and boric acid. Phenylation of 1,X-naphthyridine (X=5,6,7,and 8) with phenyllithium afforded monophenylated compounds, phenyllithium having reacted in the 2-position. Methylation of II with methylsulfinyl carbanion afforded 4,8-dimethyl-1,7-naphthyridine (XI), and the Reissert reaction of II with benzoyl chloride and potassium cyanide afforded the normal Reissert compound (XII). Insecticidal activity of V, VIII-X, and XIII-XVIII was also examined.
公益社団法人日本薬学会の論文
1976-08-25