ortho-Disubstituted F-benzenes. I. Preparation of (F-benzo)heterocyclic compounds from F-aniline and the reactions of some intermediate (F-phenyl)amino compounds.
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概要
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With the intention of achieving the selective <I>ortho</I>-disubstitution of <I>F</I>-aniline <I>via</I> intramolecular nucleophilic cyclization, syntheses of some requisite intermediate (<I>F</I>-phenyl)amino compounds and (<I>F</I>-benzo)heterocyclic compounds were investigated. 2-Phenyl-<I>F</I>-benzoxazole, 2-phenyl-<I>F</I>-benzimidazole, and 2,3-dihydro-1,4-(<I>F</I>-denz)oxazin-3-one were obtained from the respective precursors: benz-<I>F</I>-anilide, <I>N</I>-(<I>F</I>-phenyl)benzamidine, and hydroxyacet-<I>F</I>-anilide. 2-Phenyl-<I>F</I>-benzothiazole was obtained by treating benz-<I>F</I>-anilide with phosphorus pentasulfide. Hydrolytic dehalogenation of haloacet-<I>F</I>-anilide failed to give hydroxyacet-<I>F</I>-anilide, but it was obtained successfully by catalytic debenzylation of benzyloxyacet-<I>F</I>-anilide. The reactions of iodoacet-<I>F</I>-anilide with silver nitrate and acetate yielded 2-nitrate and 2-acetate, respectively. The reaction with diamminesilver(I) nitrate resulted in a reductive deiodination which gave acet-<I>F</I>-anilide. This exceptional reactivity was ascribed to the strong electron-withdrawing effect of the <I>F</I>-phenyl group.
- 公益社団法人 日本化学会の論文
著者
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Sonoda Takaaki
Research Institute Of Industrial Science Kyushu University
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Oono Yoshitsugu
Research Institute For Mathematical Sciences Kyushu University
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Kobayashi Hiroshi
Research Institute Of Industrial Science Kyushu University
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Inukai Yoshinari
Department of Organic Synthesis, Faculty of Engineering, Kyushu University 36
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Oono Yoshitsugu
Research Institute of Industrial Science, Kyushu University 86
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