アミン N-オキシドの関与する反応(第10報)ジアジン類とピリジン N-オキシドとの反応

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When a reaction is carried out with pyridine 1-oxide and platinized palladium-carbon catalyst, the 4-position of pyrimidine and 2-position of pyrazine and quinoxaline are highly reactive, and products thereby obtained are 4,4'-tripyrimidine, 2,2'-dipyrazine, tripyrazine, and 2,2'-diquinoxaline. The 2-position of pyridazine and pyrimidine, and quinazoline are entirely unreactive, while phthalazine gives a small amount of phthalonitrile. Among reactive compounds, pyrimidine and quinoxaline undergo reaction with pyrimidine, formed by deoxygenation of the N→O group, and form 4-(2'-pyridyl) pyrimidine and 2-(2'-pyridyl) quinoxaline, respectively, but a corresponding compound is not formed from pyrazine. When a hydroxyl group is introduced into the position adjacent to the ring nitrogen, 3 (2H)-pyridazinone thus formed shows reactivity and forms 6-(2'-pyridyl)-3 (2H)-pyridazinone, while 2 (1H)-pyrazinone gives a minute amount of 3-(2'-pyridyl)-2 (1H)-pyrazinone. Neither forms a dimer. 4 (3H)-Pyrimidinone and 4 (3H)-quinazolinone both form pyridine derivatives at their 2-position and corresponding dimers.
社団法人日本薬学会の論文
1978-01-25