Studies on Pyridazines. XXIV. The Reaction of Pyridazine N-Oxides and Pyridazinium Ylides with Benzyne

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概要

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• The reaction of pyridazine N-oxide (1) with benzyne produced 1-benzoxepine (5) in moderate yield, via the 1,3-cycloadduct (4). By the similar reaction, N-acetyliminopyridazinium ylide (2) and pyridazinium dicyanomethylide (3) yielded the 1,3-cycloadducts (9 and 21). The adduct (9) was transformed into the 3-vinylindazole (10) and 3-(2-acetoanilino)-pyridazine (11) by heating or treatment with sodium methoxide. Irradiation of the adduct (9) resulted in the aromatization to form indazolo[2,3-b]pyridazine (12) and in the ring contraction to form indole derivatives (13 and 14) via 1-benzazepine (19). The formation mechanism of these compounds is also discussed.

• 社団法人日本薬学会の論文
• 1975-11-25

著者

• 新井 平八郎

  Central Research Laboratories, Zeria Pharmaceutical Co., Ltd.,

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 新井 平八郎

  Central Research Laboratories Zeria Pharmaceutical Co. Ltd.

• 井下田 浩

  School Of Pharmaceutical Sciences Showa University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 長谷川 博司

  School of Pharmaceutical Sciences, Showa University

• 長谷川 博司

  School Of Pharmaceutical Sciences Showa University

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