Photocyclization of N-Chloroacetyl-2,5-dimethoxyphenethylamine. Synthesis of Pyrroloindoles

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概要

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• On irradiation in an aqueous solution, N-chloroacetyl-2,5-dimethoxyphenethylamine (1) gave 6,9-dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one (2), 7-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one (4), 4-methoxy-1-azatricyclo[6,2,1,0^<4,11>]undeca-5-ene-2,7-dione (7) and 11-methoxy-1-azatricyclo[6,2,1,0^<4,11>]undeca-7-ene-2,6-dione (8). The structure of 2,4 and 8 were determined by their spectral data. Compound 7 has also nicely assignable spectra except the ultraviolet spectrum in which no π-π band of the enone group appears above 200 nm. However, the structure of 7 has been confirmed through the conversion to pyrroloindole derivatives (11,13,14) and the deuterium exchange reaction. Compound 8 also gave other pyrroloindole derivatives (16,17). The mechanism of these rather unusual photocyclizations were finally discussed.

• 公益社団法人日本薬学会の論文
• 1975-11-25

著者

• 川森 政敏

  Organic Chemistry Research Laboratory

• 米光 宰

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 米光 宰

  北海道大学薬学部

• 米光 宰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 奥野 洋明

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 平尾 健一

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 川森 政敏

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 奥野 洋明

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 米光 宰

  北大 薬

• 平尾 健一

  Faculty Of Pharmaceutical Sciences Hokkaido University

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