2-位異項環置換-4(3H)-quinazolinone類と求電子試薬との反応

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概要

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• 2-(1-Oxido-2-pyridinio)-3-phenyl-4 (3H)-quinazolinone (1), 2-(1-oxido-2-pyridinio)-3-phenyl-4 (3H)-quinazolinone 1-oxide (4) and their control compounds, 3-phenyl-2-(2-pyridyl)-4 (3H)-quinazolinone (6) were nitrated under appropriate conditions, to give 3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone (2), 3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone 1-oxide (5) and 3-(3-nitrophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (7) as mononitro-derivatives or 6-nitro-3-(3-nitrophenyl)-2-(1-oxido-2-pyridinio)-4 (3H)-quinazolinone (3) and 6-nitro-3-(3-nitrophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (8) as dinitro-derivatives, selectively and in comparatively higher yield. Next, compound (6) was halogenated with bromine, NBS and NCS by varying reaction temperature and concentration of sulfuric acid, and by adding silver sulfate as an activator, to give 3-(3-bromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (10) and 6-bromo-3-phenyl-2-(2-pyridyl)-4 (3H)-quinazolinone (12) as monohalogenides and 3-(3,4-dibromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (11), or 6-bromo-3-(3-bromophenyl)-2-(2-pyridyl)-4 (3H)-quinazolinone (13) as dihalogenides, and further to give a derivative which was presumed to be a trihalogenide.

• 社団法人日本薬学会の論文
• 1980-04-25

著者

• 市川 正孝

  福山大学薬学部

• 市川 正孝

  熊本大学薬学部

• 久野 拓造

  熊本大学薬学部

• 久野 拓三

  熊本大学薬学部

• 村岡 敬治

  熊本大学薬学部

• 村岡 敬治

  Faculty Of Pharmaceutical Sciences Kumamoto University

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