2-<2-Furyl>-4-aza-benzimidazol | 93483-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-<2-Furyl>-4-aza-benzimidazol
• 英文别名: 2-furan-2-yl-1(3)H-imidazo[4,5-b]pyridine；2-(furan-2-yl)-1H-imidazo[4,5-b]pyridine
• CAS: 93483-98-8
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: RXGDUSPNSHCSNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-Furyl>-4-aza-benzimidazol 在 硫酸 、 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 5-(1-methyl-1H-imidazo[4,5-b]pyridine-2-yl)-furan-2-sulfonic acid
  参考文献：
  名称：

  Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine

  摘要：

  2,3-Diaminopyridine and furfural in the conditions of Weidenhagen reaction give rise to 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine, whose methylation in KOH-acetonee system affords isomeric 1-methyl-2-(furan-2-yl)-1H- and 3-methyl-2-(furan-2-yl)-3H-imidazo[4,5-b]pyridines. At the electrophilic substitution of the 1-methyl isomer (nitration, bromination, sulfation, formylation, acylation) depending on the conditions either furan ring, or pyridine fragment suffer the electrophilic attack. At its quaternization with methyl iodide in benzene N-methylpyridinium salt is obtained.

  DOI：

  10.1134/s1070428014110207
• 作为产物：
  描述：

  糠醛 、 2,3-二氨基吡啶 在 copper diacetate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以59%的产率得到2-<2-Furyl>-4-aza-benzimidazol
  参考文献：
  名称：

  Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine

  摘要：

  2,3-Diaminopyridine and furfural in the conditions of Weidenhagen reaction give rise to 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine, whose methylation in KOH-acetonee system affords isomeric 1-methyl-2-(furan-2-yl)-1H- and 3-methyl-2-(furan-2-yl)-3H-imidazo[4,5-b]pyridines. At the electrophilic substitution of the 1-methyl isomer (nitration, bromination, sulfation, formylation, acylation) depending on the conditions either furan ring, or pyridine fragment suffer the electrophilic attack. At its quaternization with methyl iodide in benzene N-methylpyridinium salt is obtained.

  DOI：

  10.1134/s1070428014110207

文献信息

• A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
  作者：Sonu Kumar、Manash P. Sarmah、Yella Reddy、Ashish Bhatt、Ravi Kant

  DOI：10.1080/00397911.2021.2001658

  日期：2022.1.2

  Abstract Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation

  摘要 取代的苯并咪唑类和嘧唑类化合物是药物化学领域中一类重要的杂环芳香族有机化合物。已经描述了取代苯并和吡啶稠合的 1H-咪唑的一步微波加速合成。从机理上讲，该反应通过取代的 2-氟硝基苯和取代的芳基胺通过形成 N-羟基中间体进行反应，该中间体在较高温度下裂解得到所需的产物。与先前描述的合成方法相比，这种方法实现了反应时间的减少、更高的产率、更清洁的反应。
• Benzimidazoles. I. 2-(Heterocyclic Substituted)benzimidazoles
  作者：Roy C. De Selms

  DOI：10.1021/jo01053a063

  日期：1962.6
• HAUEL, NORBERT;HEIDER, JOACHIM;DIEDEREN, WILLI;MEEL, JACQUES VAN
  作者：HAUEL, NORBERT、HEIDER, JOACHIM、DIEDEREN, WILLI、MEEL, JACQUES VAN

  DOI：——

  日期：——
• Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine
  作者：M. M. Elchaninov、A. A. Achkasova、I. M. Elchaninov

  DOI：10.1134/s1070428014110207

  日期：2014.11

  2,3-Diaminopyridine and furfural in the conditions of Weidenhagen reaction give rise to 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine, whose methylation in KOH-acetonee system affords isomeric 1-methyl-2-(furan-2-yl)-1H- and 3-methyl-2-(furan-2-yl)-3H-imidazo[4,5-b]pyridines. At the electrophilic substitution of the 1-methyl isomer (nitration, bromination, sulfation, formylation, acylation) depending on the conditions either furan ring, or pyridine fragment suffer the electrophilic attack. At its quaternization with methyl iodide in benzene N-methylpyridinium salt is obtained.