Studies on Diazepines. XVII. Synthesis of Monocyclic 1,3-Diazepines. (2). Substituent Effects on the Thermal Ring-conversion of 1,2-Diazepines into 1,3-Diazepines

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概要

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• The thermolysis of 1,2-diazepines (7a-f and 11) having an electron-donating substituent in the 4- or 6-position resulted in the formation of the 1,3-diazepines (9 and 12) and 2-aminopyridines (10), whereas 1,2-diazepines (7g-k) having an electron-withdrawing substituent in the same position gave only 2-aminopyridines (10) and no 1,3-diazepines. However, the thermolysis of 3-, 5-, or 7-substituted 1,2-diazepines with either an electron-donating or-withdrawing substituent did not give 1,3-diazepines. Heating of the bicyclic compounds (8) also gave the corresponding 1,3-diazepines. Based on these results, we concluded that the presence of an electron-donating substituent is essential for this ring-conversion of 1,2-diazepines into 1,3-diazepines. These substituent effects and the reaction mechanism are discussed.

• 公益社団法人日本薬学会の論文
• 1981-12-25

著者

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 円角 美智子

  School of Pharmacy, Hokuriku University

• 栗田 城治

  School of Pharmacy, Hokuriku University

• 栗田 城治

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 小島 弘一

  School of Pharmacy, Hokuriku University

• 栗田 城治

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 円角 美智子

  School Of Pharmacy Hokuriku University

• 小島 弘一

  School Of Pharmacy Hokuriku University

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