Ringspaltungsreaktion von Thiadiazolo- und Triazolopyrimidin-Derivaten

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概要

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• The ring-opening and rearrangement reaction of 7-methyl-5<I>H</I>-1,3,4-thiadiazolo[3,2-<I>a</I>]pyrimidin-5-ones (I) and the alternative isomeric 7-ones (XI) has been studied. I (R=H) and XI (R=H) gave quantitatively through N–N bond cleavage methylthiouracil (III) by treating with 5% NaOH, while they yielded 4-methyl-2-thiocyanato-6(1<I>H</I>)pyrimidone (II) by treating with liquid ammonia. By treating I and XI (R=alkyl) with 5% NaOH, the S–C bond cleaved to produce the corresponding acylaminopyrimidine derivatives (IV and IV′) and 3-aminopyrimidinethione (V and V′). The treatment of 2-hydrazino derivative (I; R=NHNH<SUB>2</SUB>) with 5% NaOH gave 1-amino-2-mercapto-7-methyl-5<I>H</I>-<I>s</I>-triazolo[1,5-<I>a</I>]pyrimidin-5-one (VIII) through ring-opening and recyclization. On the other hand, the pyrimidine moiety of I (R=Et and <I>i</I>-Pr) cleaved by the action of chlorine to afford 2-amino-1,3,4-thiadiazole (X; R=Et and <I>t</I>-Pr).

• 公益社団法人 日本化学会の論文

著者

• Okabe Takayuki

  Landwirtsckaftliche Fakultät, Kyushu Universität

• Taniguchi Eiji

  Landwirtsckaftliche Fakultät, Kyushu Universität

• Maekawa Kazuyuki

  Landwirtsckaftliche Fakultät, Kyushu Universität

関連論文

• Ringspaltungsreaktion von Thiadiazolo- und Triazolopyrimidin-Derivaten

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