Studies on Ketene and Its Derivatives. XLVIII. Reaction of Diketene with Hydroxylamine

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概要

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• The reaction of diketene with hydroxylamine was reinvestigated. Hydroxylamine, O-methylhydroxylamine and O-benzylhydroxylamine reacted with two equimolar amounts of diketene in the presence of triethylamine to give the corresponding 1-substituted 5-acetyl-6-hydroxy-4-methyl-2 (1H)-pyridones ; i.e., 1-hydroxy (VI), 1-methoxy (XIII), and 1-benzyloxy (XVI) derivatives. Treatment of O-benzylhydroxylamine with an equimolar amount of diketene in the absence of triethylamine yielded O-benzylacetoacetohydroxamic acid (XVII) in good yield. Catalytic reduction of XVII with palladium charcoal afforded an oily substance (XVIII), which was treated with dry hydrogen chloride to give 3-hydroxy-5-methylisoxazole (XIX).

• 公益社団法人日本薬学会の論文
• 1972-07-25

著者

• 南 信義

  Department of Chemistry, Research Laboratories, Teikoku Hormone Mfg. Co., Ltd.,

• 加藤 鉄三

  東北大学 薬

• 加藤 鉄三

  Pharmaceutical Institute Tohoku University

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

• 南 信義

  Pharmaceutical Institute, Tohoku University

• 南 信義

  Department Of Chemistry Research Laboratories Teikoku Hormone Mfg. Co. Ltd.

• 加藤 鉄三

  Pharmaceutical Institute. Tohoku University

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