ortho-Disubstituted F-benzenes. III. Preparation of (F-benzo)heterocyclic compounds from F-benzoic acid and F-phenol,and the reactions of some intermediary F-benzoyl- and F-phenoxy compounds.
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概要
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With the intention of achieving the selective <I>ortho</I>-substitution of <I>F</I>-benzoic acid and <I>F</I>-phenol <I>via</I> intramolecular nucleophilic cyclization, preparation of some requisite precursory <I>F</I>-benzoyl- and <I>F</I>-phenoxy compounds and their nucleophilic cyclization reactions were examined. 1,2-(<I>F</I>-Benz)isoxazol-3(2<I>H</I>)-one, 2-(<I>p</I>-tolyl)-1,2-(<I>F</I>-benz)isoxazol-3(2<I>H</I>)-one, 1,3-dimethyl(<I>F</I>-benzo)pyrimidine-2,4(1<I>H</I>,3<I>H</I>)-dione, and 1,4-(<I>F</I>-Benz)oxazin-3(2<I>H</I>)-one were obtained from the respective precursory <I>F</I>-benzohydroxamic acid, <I>N</I>-(<I>p</I>-tolyl)-<I>N</I>-hydroxy-<I>F</I>-benzamide, <I>N</I>,<I>N</I>′-dimethyl-<I>N</I>-(<I>F</I>-benzoyl)urea, and 2-(<I>F</I>-phenoxy)acetohydrazide. Attempted cyclizations of 2-(<I>F</I>-phenoxy)acetohydroxamic acid and (<I>F</I>-phenoxy) acetic acid were accompanied by simultaneous ring-opening and resulted in the formation of the identical product: (2-hydroxy-<I>F</I>-phenoxy)acetic acid. Transamidation of ethyl F-benzoate with hydroxylamine failed to give <I>F</I>-benzohydroxamic acid, which was then obtained by the catalytic debenzylation of <I>N</I>-benzyloxy-<I>F</I>-benzamide.
- 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
Research Institute of Industrial Science, Kyushu University 86
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