アミンN-オキシドの関与する反応(第7報) シッフ塩基とアミンN-オキシドとの反応

抄録

With the Schiff base as a model compound, compounds possessing an azoxymethine group were reacted with pyridine 1-oxide (IIa) and triethylamine N-oxide (IIb), in the presence of a platinated palladium-carbon catalyst. Reaction of N-benzylideneaniline (I) with IIa gave benzanilide (III) and that of I with IIb gave 2-phenylquinoline (V) and not III. Reaction of I with fumaric acid and paraldehyde, in the presence of platinated palladium-carbon catalyst gave V in 23.3% yield. Reaction of 2-benzylideneaminophenol (VII) with IIa gave a small amount of 2-phenylbenzoxazole (VIII), while that with IIb for 7 days at room temperature gave VIII in 6% yield. It is considered that oxidation becomes too strong in the reaction of VII with an N-oxide. Reaction of VII by bubbling air through its xylene solution, using the platinated palladium-carbon catalyst, results in approximately quantitative yield of VIII. These reactions were also examined with the derivatives of VII.