Reactions of 2-ethoxycarbonyl-1,3-indandione with aromatic amines, diazonium salts, and phenols.
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概要
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2-Ethoxycarbonyl-1,3-indandione (<B>1</B>) was treated with primary aromatic amines in acetic acid to afford 3-hydroxy-1-(arylimino) derivatives (<B>2</B>). Treatment of <B>1</B> with excess <I>p</I>-toluidine gave 3-tolylimino-4′-methyl-in-dancarboxanilide (<B>3</B>). With <I>o</I>− or <I>p</I>-phenylenediamine it yielded 3,3′-dihydroxy-1′-(<I>o</I>- or <I>p</I>-phenylenedinitrilo)di-2-indenecarboxylate. The tetraazacycloeicosene derivative was obtained by the action of <I>p</I>-phenylenediamine on <B>1</B> in a 1:1 molar ratio. In boiling toluene <B>1</B> gave the corresponding 2-carboxanilides (<B>8</B>) which cyclized to the diazepinone or to the quinolone. The coupling of <B>1</B> and <B>8</B> with diazonium salts was also investigated. The condensation of <B>1</B> with phenols afford <B>14</B>, which were hydrolysed to 3-aryl-1-indenones.
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著者
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Afsah El-Sayed
Department of Chemistry, Faculty of Science, Mansoura University
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Zimaity Tawfik
Department of Chemistry, Faculty of Science, Mansoura University