Reactions Concerned in Tertiary Amine N-Oxides. X. Reactions of Diazines with Pyridine N-Oxide

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Other Title
  • 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
  • アミンN-オキシドの関与する反応-10-ジアジン類とピリジンN-オキシドとの反応
  • アミン N オキシド ノ カンヨスル ハンノウ 10 ジアジンルイ ト ピリジ

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Description

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.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 98 (1), 67-71, 1978

    The Pharmaceutical Society of Japan

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