2-methyl-2H-triazolo<4,5-f>quinoline | 226073-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methyl-2H-triazolo<4,5-f>quinoline
• CAS: 226073-65-0
• 化学式: C₁₀H₈N₄
• 分子量: 184.2
• InChiKey: SUBZKTFTNCJVJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-methyl-2H-triazolo<4,5-f>quinoline 在 硫酸 、 potassium nitrate 作用下， 反应 12.0h， 以37%的产率得到2-methyl-5-nitro-2H-triazolo<4,5-f>quinoline
  参考文献：
  名称：

  Synthesis of Triazolo[4,5-f]quinolines. An Unusual Case of Displacement of Nitro Group in the Reaction of 8-Acetylamino-6-chloro-5-nitroquinoline with Hydrazine and Methylhydrazine

  摘要：

  Nitration of 1H-, 3-methyl- and 2-methyltriazolo[4,5-f]quinolines (6a-c) as a way to obtain the desired 4-aminotriazolo[4,5-f]quinolines (4) for a medicinal chemistry project was successful only in the case of 6c. Attempted building up of the triazole ring starting from 8-acetylamino-6-chloro-5-nitroquinoline (8) with ammonia, hydrazine and methylhydrazine at 150 degrees C in ethanol failed, However, the results obtained from these reactions allowed us to observe that, during nucleophilic aromatic substitution of chlorine by these bases an unusual displacement of the nitro group by hydrogen occurred. Comparison of these results with those obtained using different substrates allowed us to evaluate the influence of both para-acetylamino group and pyridine ring in this type of nucleophilic aromatic substitution.

  DOI：

  10.3987/com-98-s(h)34
• 作为产物：
  描述：

  2-methyl-2H-benzotriazol-5-amine 、 甘油 在 arsenic pentoxide hydrate 、 硫酸 作用下， 反应 6.0h， 以51%的产率得到2-methyl-2H-triazolo<4,5-f>quinoline
  参考文献：
  名称：

  Synthesis of Triazolo[4,5-f]quinolines. An Unusual Case of Displacement of Nitro Group in the Reaction of 8-Acetylamino-6-chloro-5-nitroquinoline with Hydrazine and Methylhydrazine

  摘要：

  Nitration of 1H-, 3-methyl- and 2-methyltriazolo[4,5-f]quinolines (6a-c) as a way to obtain the desired 4-aminotriazolo[4,5-f]quinolines (4) for a medicinal chemistry project was successful only in the case of 6c. Attempted building up of the triazole ring starting from 8-acetylamino-6-chloro-5-nitroquinoline (8) with ammonia, hydrazine and methylhydrazine at 150 degrees C in ethanol failed, However, the results obtained from these reactions allowed us to observe that, during nucleophilic aromatic substitution of chlorine by these bases an unusual displacement of the nitro group by hydrogen occurred. Comparison of these results with those obtained using different substrates allowed us to evaluate the influence of both para-acetylamino group and pyridine ring in this type of nucleophilic aromatic substitution.

  DOI：

  10.3987/com-98-s(h)34