Studies on the N-Oxides of π-Deficient N-Heteroaromatics. XXXIV. A Novel Synthesis of Substituted Indoles by Photochemical Ring Contraction of 3,1-Benzoxazepines

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概要

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• A novel photochemical ring-contraction reaction of 5-unsubstituted 3,1-benzoxazepines and their 5-halogeno or carboxyl derivatives to yield 3-formylindoles in an aprotic solvent is reported. This ring contraction was successfully extended to oxazepines having an alkoxycarbonyl function at the 5-position to give the indoles having this function at the 3-position. Though most of the oxazepines underwent the ring-contraction reaction only on irradiation at 254 nm, 5-carboxy derivatives or their esters afforded the ring-contraction products even at ≥ 300 nm. The intermediacy of 3H-indole species in these photochemical ring-contraction reactions was demonstrated by the isolation of methyl 3-acetyl-2-phenyl-3H-indole-3-carboxylate during the photolysis of methyl 4-methyl-2-phenyl-3,1-benzoxazepine-5-carboxylate. It was found that this 3H-indole afforded methyl 6-and 4-acetyl-2-phenyl-indole-3-carboxylates upon further irradiation. The mechanism of this acetyl migration is discussed based on the result of the photochemical acetyl migration of methyl 1-acetyl-2-phenylindole-3-carboxylate.

• 公益社団法人日本薬学会の論文
• 1980-04-25

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

• 木股 利彦

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 木股 利彦

  Faculty Of Pharmaceutical Sciences Kanazawa University:(present Address)jyoko Chemical Co. Ltd.

• 川合 信次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 春恵

  Faculty Of Pharmaceutical Sciences Kanazawa University

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