Studies on Pyrazolo [3,4-d] pyrimidine Derivatives. XIII. Aryl Migration of 4-Aroyl-1H-pyrazolo [3,4-d] pyrimidines to 4-Aryl-4,5-dihydro-1H-pyrazolo [3,4-d] pyrimidine-4-carboxylic Acids

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概要

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• When a mixture of 4-aroyl-1-phenyl-1 H-pyrazolo [3,4-d] pyrimidines (3) and sodium hydroxide in dimethyl sulfoxide (DMSO) was stirred for 1h at room temperature, migration of the aryl group to the 4-position occurred, i. e., the benzilic acid rearrangement, resulting in the formation of 4-aryl-4,5-dihydro-1-phenyl-1H-pyrazolo [3,4-d] pyrimidine-4-carboxylic acids (4). Potassium ferricyanide oxidized the carboxylic acids (4) to the corresponding 4-aryl-1-phenyl-1H-pyrazolo [3,4-d] pyrimidines (5) with elimination of carbon dioxide. Reaction of 5 with sodium hydroxide in DMSO caused ring fission of the pyrazole portion, to give the corresponding 6-anilino-4-aryl-5-pyrimidinecarbonitriles (11).

• 公益社団法人日本薬学会の論文
• 1983-11-25

著者

• 林 英作

  Shizuoka College of Pharmacy

• 東野 武郎

  Shizuoka College of Pharmacy

• 林 英作

  School Of Pharmaceutical Sciences University Of Shizuoka

• 竹元 万寿美

  Shizuoka College of Pharmacy

• 松下 保彦

  Shizuoka College of Pharmacy

関連論文

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