Syntheses of nitrogen-containing heterocyclic compounds. XXIII. Reaction of naphthyridine derivatives, with special reference to that of 1,7-naphthyridine.

Abstract

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.