Pyranoindole and Thiopyranoindole. Oxidative Cyclization of 3-Indolepropanol and 3-Indolepropanethiol with N-Bromosuccinimide, N-Chlorosuccinimide, and Singlet Oxygen

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概要

• 論文の詳細を見る

• Oxidative cyclization of 3-indolepropanethiol (6) and 3-indolepropanol (9) with N-bromosuccinimide or N-chlorosuccinimide (NCS) gave the corresponding thiopyrano-[2,3-b] indole (7) and pyrano [2,3-b] indole (10) in good yields. Reaction of 7 with NCS in carbon tetrachloride gave an unstable chloroindolenine (18) which transformed to a spirooxindole (19) on treatment with ethanolic hydrochloric acid. Reaction of 7 with NBS in carbon tetrachloride gave 7-bromo derivative (20) via the 3-bromoindolenine. Similarly pyranoindole (10) gave a spirooxindole (23) in good yield on treatment with NCS in methylene chloride followed by the addition of ethanolic hydrochloric acid. On the other hand reaction of 9 with two equivalents of NCS gave 23 and dichlorooxindole (24). Dye-sensitized photooxygenation of 3-indolepropanol (9) in benzene gave 4a-hydroxypyrano [2,3-b] indole instead of 10.

• 公益社団法人日本薬学会の論文
• 1978-12-25

著者

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

• 三浦 偉俊

  Faculty Of Pharmaceutical Sciences Chiba University

• 村田 良一

  Faculty Of Pharmaceutical Sciences Chiba University

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