Effects of <I>N</I>-Acyl- and <I>N</I>-<I>s</I>-Triazinyl Groups on the Rearrangement of <I>S</I>-(<I>s</I>-Triazinyl)-2-aminothiophenols and <I>O</I>-(<I>s</I>-Triazinyl)-2-aminophenols

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概要

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• <I>S</I>-<I>s</I>-Triazinyl-2-aminothiophenols (I) containing methoxyl and/or dimethylamino groups in the <I>S</I>-triazine nucleus gave disulfides of <I>N</I>-<I>s</I>-triazinyl-2-aminothiophenols upon the S→N migration of the <I>s</I>-triazinyl group in the presence of acid; the rate of S→N migration was slow compared to that of the O→N migration of the corresponding <I>O</I>-<I>s</I>-triazinyl-2-aminophenol. On acylation or <I>s</I>-triazinylation, <I>S</I>-dimethoxy-<I>s</I>-triazinyl-2-aminothiophenol (I–1) and <I>O</I>-dimethoxy-<I>s</I>-triazinyl-2-aminophenol (II-1) gave <I>N</I>-acyl-<I>N</I>-<I>s</I>-triazinyl- or <I>N</I>,<I>N</I>-bis (<I>s</I>-triazinyl) derivatives upon the S→N or O→N migration of the <I>s</I>-triazinyl group. However, <I>S</I>-dimethylaminomethoxy-<I>s</I>-triazinyl-2-aminothiophenol (I–2), <I>S</I>-bis[(dimethylamino)-<I>s</I>-triazinyl]-2-aminothiophenol (I–3) and the corresponding derivatives of <I>o</I>-aminophenol gave <I>N</I>-acyl- or <I>N</I>-<I>s</I>-triazinyl derivatives, wihtout any migration of the <I>s</I>-triazinyl group, by acylation or <I>s</I>-triazinylation. The facility of the rearrangement of these <I>N</I>,<I>S</I>-bis-(<I>s</I>-triazinyl)-2-aminothiophenols and <I>N</I>,<I>O</I>-bis(<I>s</I>-triazinyl)-2-aminophenols depended not only upon the substituents in <I>S</I>- or <I>O</I>-<I>s</I>-triazine nucleus, but also upon the substituents in the <I>N</I>-<I>s</I>-triazine nucleus; the substituents in the <I>N</I>-<I>s</I>-triazine nucleus of strong electron-attracting and of strong electron-donating substances were not appropriate for the rearrangement in the presence of alkali to give disulfides of <I>N</I>-<I>s</I>-triazinyl-2-aminothiophenols (III–I) or <I>N</I>-<I>s</I>-triazinyl-2-aminophenols (III–II).

• 公益社団法人 日本化学会の論文

著者

• Hasegawa Yasushi

  Department Of Applied Chemistry Muroran Institute Of Technology

• KURODA Toshio

  Department of Cardiology, Jichi Medical School

• Matsui Kohji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Hasegawa Yasushi

  Department of Chemistry, Faculty of Engineering, Gunma University

• Shiojima Takeo

  Department of Chemistry, Faculty of Engineering, Gunma University

• Ohkawa Sohei

  Department of Chemistry, Faculty of Engineering, Gunma University

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