Studies of heterocyclic compounds. VIII. Synthesis and tautomerism of 2-hydroxypyrazolo(1,5-a)pyridine.

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概要

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• 2-Hydroxypyrazolo[1,5-<I>a</I>]pyridine (I) was synthesized by reaction of ethyl 2-pyridylacetate (IV) with hydroxylamine-<I>O</I>-sulfonic acid. I was shown to undergo nitrosation, nitration and bromination at C-3 position. Methylation of I with diazomethane gave 2-methoxypyrazolo[1,5-<I>a</I>]pyridine (V), while methylation of I with dimethyl sulfate gave a mixture of V and 1-methyl-1,2-dihydropyrazolo[1,5-<I>a</I>]pyridin-2-one (VI). The enol form was found to be predominant tautomeric species of I in solution. Treatment of I with acetic anhydride afforded 2-acetoxypyrazolo[1,5-<I>a</I>]pyridine (XIII) exclusively. 1-Acetyl-1,2-dihydropyrazolo[1,5-<I>a</I>]pyridin-2-one (XIV) dose not seem to intervene in the formation of thermally stable <I>O</I>-acetylated product (XIII).

• 公益社団法人 日本化学会の論文

著者

• Miyasaka Tadashi

  School Of Pharmaceutical Sciences Showa University

• Ochi Hisao

  School of Pharmaceutical Sciences, Showa University

• Kanada Kiyoshi

  Research and Developing Section, Horiuchi Itaro Co. Ltd.

• Arakawa Kiichi

  School of Pharmaceutical Sciences, Showa University

関連論文

• Stereoselective Synthesis of 4'-α-Alkylcarbovir Derivatives Based on an Asymmetric Synthesis or Chemoenzymatic Procedure
• Studies of heterocyclic compounds. VIII. Synthesis and tautomerism of 2-hydroxypyrazolo(1,5-a)pyridine.
• Studies of heterocyclic compounds. XII. Structures of acetylated products of 5-hydroxy-4-(2-hydroxyethyl)-3-methylpyrazole.

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