2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-β-carbolines. : The Pictet-Spengler Reaction of N-Hydroxytryptamine with Aldehydes

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概要

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• The Pictet-Spengler reaction of N-hydroxytryptamine (6) with various aldehydes was examined. Reduction of 3-(2-nitroethyl) indole (5) with aluminum amalgam gave 6,which was not so stable and was readily oxidized to the azoxy compound (10) in solution under an oxygen atmosphere. Reaction of 6 with saturated aldehydes gave the corresponding nitrones (11b, c) without an acid catalyst at room temperature, while the reaction with α, β-unsaturated aldehydes provided nitrones (11d, e, f) in the presence of trifluoroacetic acid. Cyclization of the nitrones with trifluoroacetic acid in methylene chloride gave the 2-hydroxy-1,2,3,4-tetrahydro-β-carbolines (2) in good yields. The cyclization of the saturated nitrones proceeded rapidly, whereas the similar reaction of the unsaturated nitrones was slow. Direct Pictet-Spengler reaction of 6 with aldehydes in methylene chloride in the presence of trifluoroacetic acid gave 2a, b, c in excellent yields. Dehydration of the 2-hydroxy-β-carboline (2b) with trifluoroacetic anhydride in benzene gave the 3,4-dihydro-β-carboline (15). 6-Bromo-5-methoxy-N-hydroxytryptamine (25) was prepared from 3-bromo-4-methyoxyaniline (17) via the indole (22). The Pictet-Spengler reaction of 25 with isovaleraldehyde gave the 2-hydroxy-tetrahydro-β-carboline (26).

• 社団法人日本薬学会の論文
• 1990-01-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 劉 進軍

  School of Pharmacy, Shanghai Medical University

• 長谷川 敦

  Faculty of Pharmaceutical Sciences, Chiba University

• 劉 進軍

  Faculty of Pharmaceutical Sciences, Chiba University

• 劉 進軍

  School Of Pharmacy Shanghai Medical University

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

• 長谷川 敦

  Faculty Of Pharmaceutical Sciences Chiba University

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