Reactions of 1-Naphthols with π-Acceptor p-Benzoquinones : Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation

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概要

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• We investigated the reactions of various 1-naphthols (NPOHs ; 1) with p-benzoquinones (Qs), such as 1, 4-benzoquinone (BQ) and p-chloranil (CA), as π-electron acceptors. With electron-rich NPOHs 1a-c, oxidative biaryl coupling and subsequent dehydrogenation reaction took place selectively to give the corresponding 2, 2'-binapthyl-1, 1'-quinones 3a-c in excellent yield. In the case of electron-deficient NPOHs 1e, f, two different types of reactions occurred in the presence of SnCl_4 and ZrO_2 under similar conditions : SnCl_4 mediated oxidative dimerization and trimerization of NPOH, while ZrO_2 promoted electrophilic arylation of Qs with NPOH. The resulting products 3 would be useful synthetic intermediates for naturally occurring diosindigo B, biramentaceone and violet-quinone.

• 公益社団法人日本薬学会の論文
• 2005-02-01

著者

• Okamoto I

  Showa Pharmaceutical University

• Okamoto Iwao

  Fujisaki Institute Hayashibara Biochemical Laboratories Inc.

• TAKEYA Tetsuya

  Showa College of Pharmaceutical Sciences

• KOTANI Eiichi

  Showa Pharmaceutical University

• Takeya T

  Showa Pharmaceutical University

• Kotani E

  Showa Pharmaceutical University

• Kotani Eiichi

  Showa College Of Pharmaceutical Sciences

• Okamoto Iwao

  Showa Pharmaceutical University

• KONDO Hiromu

  Showa Pharmaceutical University

• OTSUKA Tsuyoshi

  Showa Pharmaceutical University

• DOI Hirohisa

  Showa Pharmaceutical University

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