Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 6. Synthetic Procedure for 4-, 5-, 6-, or 7-Alkoxy- and Hydroxyindole Derivatives

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概要

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• A novel method for the preparation of indole derivatives that are alkoxy- and hydroxy-substituted in the benzene portion of the indole nucleus is described. The acid-induced cyclization reaction of (arylsulfonyl)pyrrole derivatives (4a, 5b, and 5a) in the presence of an appropriate alcohol gave 4-, 5-, 6-, and 7-alkoxyindole derivatives (13 and 28), respectively, where the alkoxy group was originated from the alcohol employed. As an application of the present method, a short and efficient synthesis of two dopamine agonists (34 and 44) was attained by treating appropriately functionalized pyrrole derivatives (38 and 41) with an acid in the presence of 1,3-propanediol, followed by deprotection of alkoxy function, and subsequent reduction with lithium aluminum hydride. A reaction mechanism is also suggested for the formation of an unusual product, 4-[2-(diprophlamino)-1-hydroyethyl]-6-hydroxyindole (46) in the reduction of N, N-dipropyl-(6-hydroxy-1-phenylsulfonyl)indole-4-acetamide (40).

• 公益社団法人日本薬学会の論文
• 1992-09-25

著者

• 冨士 雅弘

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 村竹 英昭

  Research Foundation Itsuu Laboratory

• 夏目 充隆

  Research Foundation Itsuu Laboratory

• 村竹 英昭

  Res. Foundation Itsuu Lab. Tokyo Jpn

• 冨士 雅弘

  Research Foundation Itsuu Laboratory

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