Studies on the N-Oxides of π-Deficient N-Heteroaromatics. XXXVI. Photochemical and Thermal Michael Reactions of Alcohols with Methyl 2-Phenyl-3,1-benzoxazepine-5-carboxylate and Its Derivatives

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概要

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• Irradiation (≥300 nm) of methyl 2-phenyl-3,1-benzoxazepine-5-carboxylate in an alcohol afforded the Z-isomer of methyl 3-alkoxy-2-(2-benzamidophenyl)-acrylate as the major addition product. In contrast, thermal reaction of the oxazepine with a primary alcohol in the presence of triethylamine led to the exclusive formation of the corresponding E-isomer. The same kinds of Michael addition products were also obtained stereoselectively from 3,1-benzoxazepines having an acetyl group at the 5-position under these conditions. The interrelation between the stereoisomers obtained from the oxazepine and an alcohol under these two conditions was established by photochemical equilibration, and the stereochemistry of the two isomers was determined by proton magnetic resonance spectroscopy. An explanation is proposed for the observed stereoselectivities in the two kinds (photochemical and thermal) of reactions.

• 公益社団法人日本薬学会の論文
• 1982-01-25

著者

• 金子 主税

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 染井 正徳

  Faculty of Parmaceutical Sciences, Kanazawa University

• 藤井 春恵

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 林 令子

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 橋場 和彦

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 金子 主税

  Pharmaceutical Institute Tohoku University

• 唐沢 良夫

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 川合 信次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 若井 ますえ

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 藤井 春恵

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 若井 ますえ

  Faculty Of Pharmaceutical Sciences Kanazawa University

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