Oxidation of 1-Acylindoles with Oxodiperoxomolybdenum (VI), MoO_5・HMPA. Preparation of 2,3-Dihydroxyindoline and Indoxyl Derivatives

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概要

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• The oxidation of 1-acylindoles, 1,15,20,and 22,with (hexamethylphosphoramide) oxodiperoxomolybdenum (VI), MoO_5・HMPA, in dry methanol gives a variety of products depending on the indole substituents ; trans- and cis-1-acyl-3-hydroxy-2-methoxyindolines 2 and 3 are obtained from 2,3-unsubstituted 1-acylindoles 1,1-acetyl-2-hydroxy-3-methoxy-3-methylindoline (16) from 1-acetyl-3-methylindole (15), 1-acetyl-2,3-dihydroxy-2,3-dimethylindoline (21) from 1-acetyl-2,3-dimethylindole (20), and 1-acetyl-2-hydroxy-2-methylindoxyl (23) from 1-acetyl-2-methylindole (22). Reaction of 2 and 3 with acids gives 1-acylindoxyl 10,respectively, while reaction of 16 with the acid gives 3-methyloxindole (19). Treatment of 3-acetoxy-1-acetyl-2-methoxyindoline (5) with stannic chloride gives 1-acetylindoxyl (10a) and 1-acetyl-3-chloroindole (14).

• 公益社団法人日本薬学会の論文
• 1984-10-25

著者

• 川崎 知己

  明治薬科大学

• 坂本 正徳

  Meiji College of Pharmacy

• 川崎 知己

  Meiji College of Pharmacy

• 鈴木 孝子

  Meiji College Of Pharmacy

• 簡 俊生

  Meiji College of Pharmacy

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