Ring Transformations of 6H-Cyclopropa [e] pyrazolo [1,5-a] pyrimidine. III. Synthesis and X-Ray Crystal Structure Determination of a 1-Pyrazol-3-ylpyrrole-2-carboxylic Acid

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概要

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• Ring transformations and ring expansions of ka-acetyl-5a, 6a-dihydro-6a-ethoxy-carbonyl-6H-cyclopropa [e] pyrazolo [1,5a] pyrimidines (3,4 and 5) are described. For example, treatment of 4a with potassium hydroxide in ethanol gave 4-acetyl-1-(4-cyanopyrazol-3-yl)-5-methylpyrrole-2-carboxylic acid (7a), the structure of which was confirmed by X-ray crystal structure determination. On the other hand, it was found that 3a reacted with ethanol, with ethanol in the presence of potassium hydroxide, or with acetic acid to give 7,8-dihydro-8-ethoxy (or acetoxy)-4H-pyrazolo [1,5-a] [1,3] diazepines (17,11 or 24,respectively) in moderate yields. Furthermore, when aqueous dioxane was used as the reaction medium, 3a was transformed to ethyl 6-pyrazolo [1,5-a] pyrimidinepyruvate (22), which was found to exist as a mixture of keto and enol tautomers. The mechanism of formation of these products is discussed.

• 公益社団法人日本薬学会の論文
• 1981-11-25

著者

• 石田 寿昌

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 井上 正敏

  Osaka University of Pharmaceutical Sciences

• 井上 正敏

  Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences

• 那須 啓子

  Osaka College of Pharmacy

• 谷 力

  Osaka College of Pharmacy

• 栗原 拓史

  Osaka College Of Pharmacy

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