Studies on Pyrazolo[3,4-d]pyrimidine Derivatives. XV. Reactions Involving the Formation of the Anion of the Reissert Compound Derived from 1H-Pyrazolo[3,4-d]pyrimidine(Organic,Chemical)

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概要

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• The anion (A) of the Reissert compound (1, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile) was found to react with electrophiles in two ways. One is nucleophilic attack of the anion A. The other is self-decomposition of the anion A. Thus, A underwent nucleophilic attack with aromatic and aliphatic aldehydes (4a-j), resulting in the formation of the corresponding α-aryl (or alkyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylmethyl benzoates (6a-j) together with 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (2), the 4,4'-dimer (7) of 2, O-benzoylaroins (8a-d), and O-benzoylcyanohydrins (9e-j). Nucleophilic substitution took place in the reaction of A with 2,4-dinitrochlorobenzene (14a) and methyl iodide (14d), giving the 4-(2,4-dinitrophenyl) derivative (17a) of 2 and 5,7-dibenzoyl-4-methyl-1-phenyl-4-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-d]pyrimidine-6-carbo-nitrile (19), respectively. However, the anion A did not react with other aryl (or alkyl) halides (14b, c, e), ketones (11a, b), 2-alkenonitriles (21a, b), and dimethyl acetylenedicarboxylate (22), and underwent the known self-decomposition, resulting in the formation of products such as 2, 7, the cyano derivative (18) of 2, and the ester 6a.

• 社団法人日本薬学会の論文
• 1987-10-25

著者

• 東野 武郎

  School Of Pharmaceutical Sciences University Of Shizuoka

• 佐藤 進

  Central Research Laboratories, S S Pharmaceutical Co., Ltd.,

• 宮下 晶

  School Of Pharmaceutical Sciences University Of Shizuoka

• 佐藤 進

  Department Of Pharmacology Pharmaceutical Institute Tohoku University

• 香取 達彦

  Central Research Laboratories, SS Pharmaceutical Co., Ltd.

• 香取 達彦

  Central Research Laboratories S S Pharmaceutical Co. Ltd.

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