4-Cyano-5-hydroxy-3-(4-methoxyphenyl)-1-methylpyrazole | 139347-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Cyano-5-hydroxy-3-(4-methoxyphenyl)-1-methylpyrazole
• CAS: 139347-64-1
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: UKIFRUVBDRVAJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.1±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)-1-methyl-4,5-dihydro-1H-pyrazol-5-one 在 sodium azide 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 4-Cyano-5-hydroxy-3-(4-methoxyphenyl)-1-methylpyrazole
  参考文献：
  名称：

  Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

  摘要：

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.

  DOI：

  10.1021/jo00033a039