Studies on Ketene and Its Derivatives. CI. Reaction of Diketene with 4-Amino-methylpyridine 1-Oxides

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• The reaction of diketene with 4-amino-methylpyridine 1-oxides was examined. 4-Aminopyridine 1-oxide (1a) and 4-amino-3-methylpyridine 1-oxide (1c) reacted with diketene in the presence of triethylamine at 0--5° to give the corresponding substituted 2,6-dimethyl-4-pyrone-3-carboxamides ; i. e., N-(1-oxido-4-pyridyl) (3a) and N-(3-methyl-1-oxido-4-pyridyl) (3c) compounds. The reaction of diketene with 4-aminomethylpyridine 1-oxides (1b, d, and e) afforded 4-acetoacetamindopyridine 1-oxides (2b, d, and e) under the same conditions. However, the reaction of diketene with 4-aminopyridine 1-oxides (1f and g) possessing an ethyl group at the 3-position gave N-(3-ethyl-1-oxido-4-pyridyl)-2-acetyl-3,5-dimethyl-phenol-4-carboxamides (5f and g), together with N-(3-ethyl-1-oxido-4-pyridyl)-2,6-dimethyl-4-pyrone-3-carboxamides (3f and g). The mechanism of formation of compounds 5f and g is discussed.

• 社団法人日本薬学会の論文
• 1980-07-25

著者

• 和賀井 昭博

  Pharmaceutical Institute Tohoku University

• 加藤 鉄三

  Pharmaceutical Institute, Tohoku University

• 田中 倫子

  Pharmaceutical Institute Tohoku University

• 加藤 鉄三

  Pharmaceutical Institute Tohoku University

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 播磨谷 健蔵

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

• 播磨谷 健蔵

  Pharmaceutical Institute School Of Medicine Keio University

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