The transition metal-catalyzed N-heterocyclization. A reductive transformation of aminonitroarenes and dinitroarenes into phenanthroline derivatives using aliphatic aldehydes under carbon monoxide pressure.
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概要
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The Catalytic <I>N</I>-heterocyclization of aminoarenes and dinitroarenes using aliphatic <I>n</I>-C<SUB>3</SUB>–C<SUB>5</SUB> aldehydes was carried out at 180 °C under the pressure of carbon monoxide (70 atm at room temperature) in the presence of RhCl(PPh<SUB>3</SUB>)<SUB>3</SUB> and PdCl<SUB>2</SUB> as a binary catalyst system. The reaction of <I>p</I>-nitroaniline with propanal, butanal, and pentanal gave 3,8-diethyl-2,9-dimethyl-4,7-phenanthroline, 2,9-diethyl-3,8-dipropyl-4,7-phenanthroline, and 3,8-dibutyl-2,9-dipropyl-4,7-phenantroline in 43, 57, and 54% yields respectively. On the other hand, <I>m</I>-nitroaniline and <I>o</I>-nitroaniline gave 1,7-phenanthroline and imidazole derivatives in rather low yields (21 and 24%) under the reaction conditions employed.
- 公益社団法人 日本化学会の論文
著者
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Tsuji Yasushi
Department Of Energy And Hydrocarbon Chemistry Graduate School Of Engineering Kyoto University
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Watanabe Yoshihisa
Department Of Basic Geriatrics Graduate School Of Medical Science Kyoto Prefectural University Of Medicine
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SUZUKI Naoki
Department of Agricultural Chemistry, Ibaraki University
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