Studies on Diazepines. VIII. Syntheses and Rearrangements of 3H-1,2-Pyrido- and 3H-1,2-Thieno-diazepines

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概要

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• The previously unknown 3H-1,2-pyrido-(3a, b) and 3H-1,2-thieno-(3c, d) diazepines were prepared from the corresponding 1H-isomers. Treatment of 3 with bases or acids resulted in tautomerization to give the 1H-diazepines (1), and photolysis of 3 afforded the condensed 3-vinylpyrazoles (4). However, thermolysis of the pyridodiazepines (3a, b) gave 4a, b, whereas the thienodiazepines (3c, d) gave the thienylpyrazoles (5) on irradiation via a [1,5] hydrogen shift in the diazepine ring ; this mechanism was confirmed by a deuterium-labelling experiment. The 3-acetoxy-(13a) and 3-methoxy-(13b) 3H-1,2-thienodiazepines were also prepared, and their photolysis afforded 3-vinylpyrazoles (14). However, thermolysis or base treatment of 13 resulted in loss of nitrogen to give compounds (15) and (16).

• 社団法人日本薬学会の論文
• 1979-09-25

著者

• 沢西 啓之

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 沢西 啓之

  School of Pharmacy, Hokuriku University

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 円角 美智子

  School of Pharmacy, Hokuriku University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 円角 美智子

  School Of Pharmacy Hokuriku University

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