Preparation of Alkyl-Substituted Indoles in the Bezene Portion. Part 5. Efficient Preparative Procedure for 4-Substituted Indole Derivatives

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概要

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• An effective and short synthetyic method for 4-substituted indole derivatives was developed based on the two sequential reactions, i.e. nucleophilic addition of carbanions to common precursor molecules, 3-(1,3-dioxolan-2-yl)-1-[1-(phenylsulfonyl)- and 1-[(4-methylphenyl)sulfonyl]-3-pyrrolyl]-1-propanones (5a, b), followed by the acid-induced cyclization reaction of the resulting adducts to form 4-substituted 1-(phenylsulfonyl)- and 1-[(4-methylphenyl)-sulfonyl]indole derivatices (4a, b). This new method makes it possible resadily to synthesize imoportant intermediates, such as methyl 1-(phenylsulfonyl)indole-4-carboxylate (15), 4-formyl-1-(phenylsulfonyl)indole (16), and methyl 1-(phenylsulfonyl)indole-4-acetate (17) for numerous indole alkaloids, as well as a potent dopamine agonist, 4-[2-(diprophlamino)ethyl]indole (21).

• 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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