Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation
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Accession number;05A0106839
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| Title;Reactions of 1-Naphthols with .PI.-Acceptor p-Benzoquinones: Oxidative Aryl Coupling vs. Non-Oxidative Electrophilic Arylation |
| Author;
TAKEYA T
(Showa Pharmaceutical Univ., Tokyo, Jpn)
KONDO H
(Showa Pharmaceutical Univ., Tokyo, Jpn)
OTSUKA T
(Showa Pharmaceutical Univ., Tokyo, Jpn)
DOI H
(Showa Pharmaceutical Univ., Tokyo, Jpn)
OKAMOTO I
(Showa Pharmaceutical Univ., Tokyo, Jpn)
KOTANI E
(Showa Pharmaceutical Univ., Tokyo, Jpn)
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Journal Title;Chem Pharm Bull
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Journal Code:G0504A
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ISSN:0009-2363
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VOL.53;NO.2;PAGE.199-206(2005)
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| Figure&Table&Reference;TBL.2, REF.54 |
| Pub. Country;Japan |
| Language;English |
| Abstract;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 .PI.-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 SnCl4 and ZrO2 under similar conditions: SnCl4 mediated oxidative dimerization and trimerization of NPOH, while ZrO2 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. (author abst.) |
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