Studies of Heterocyclic Compounds. I. Structures of Acetylated Products of 3-Methylpyrazol-5-one

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概要

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• Acetylation of 3-methylpyrazol-5-one (I) with acetic anhydride produces five acetates according to the reaction condition : by heating in the presence of concentrated sulfuric acid 4-acetyl-3-hydroxy-5-methylpyrazole (II) ; by heating several minutes crystalline monoacetate, 2-acetyl-3-hydroxy-5-methylpyrazole (IV) and oily diacetate, 3-acetoxy-2-acetyl-5-methylpyrazole (V) ; by heating for several hours crystalline diacetate, 3-acetoxy-1-acetyl-5-methylpyrazole (VI) ; and by heating in the presence of pyridine monoacetate, 1-acetyl-3-hydroxy-5-methylpyrazole (VII). Basic hydrolysis of the acetates (IV, V, VI, and VII) gives the starting pyrazolone (I). The enol-acetate moiety of the diacetate (V or VI) is more susceptible to hydrolysis under mild condition to give the corresponding N-monoacetate (IV or VII). Inspection by nuclear magnetic resonance spectroscopy of the acetates reveals that the chemical shift of C_5-methyl grouping is observed at approximately 0.3 ppm lower field when acetylated at the adjacent nitrogen atom.

• 公益社団法人日本薬学会の論文
• 1974-01-25

著者

• 宮坂 貞

  School Of Pharmaceutical Sciences Showa University

• 荒川 基一

  School of Pharmaceutical Sciences, Showa University

• 越智 久雄

  昭和大学薬学部

• 越智 久雄

  School Of Pharmaceutical Sciences Showa University

• 荒川 基一

  School Of Pharmaceutical Sciences Showa University

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