Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XIV. : Preparation and Reactions of 1-Phenyl-1H-pyrazolo-[3,4-d]pyrimidine Reissert Compound
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概要
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The Reissert reaction of 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (4) in anhydrous methylene chloride using benzoyl chloride, trimethylsilyl cyanide, and a catalytic amount of aluminium chloride gave the corresponding Reissert compound (3,5-benzyol-4,5-dihydro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile) in 95% yield.The alkaline hydrolysis of 3 in methanol resulted in the formation of 4,benzoic acid (7), and the 4,4'-dimer (9) of 4. The acid hydrolysis in dimethyl sulfoxide and in methanol proceeded with ring fission to give 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetonitrile (13), the acetamide (14), and the acetate (15). Compound 3 reacted with sodium hydride in dimethylformamide to give 4,9,1-phenyl-1H-pyrazolo[3,4-d]-pyrimidine-4-carbonitrile (20), α, 1-diphenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylmethyl benzoate (21), and O-benzoylmandelonitrile (22).In the present paper, we compare the chemical properties of 3 with those of the isoquinoline Reissert compound (1,2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile).
- 社団法人日本薬学会の論文
- 1986-11-25
著者
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佐藤 進
Central Research Laboratories, S S Pharmaceutical Co., Ltd.,
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東野 武郎
Shizuoka College of Pharmacy
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佐藤 進
Department Of Pharmacology Pharmaceutical Institute Tohoku University
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宮下 晶
Shizuoka College of Pharmacy
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香取 達彦
Central Research Laboratories, SS Pharmaceutical Co., Ltd.
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香取 達彦
Central Research Laboratories S S Pharmaceutical Co. Ltd.
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