6-methyl-3-nitroso-2-(p-tolyl)imidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-methyl-3-nitroso-2-(p-tolyl)imidazo[1,2-a]pyridine
• 英文别名: 6-Methyl-2-(4-methylphenyl)-3-nitrosoimidazo[1,2-a]pyridine；6-methyl-2-(4-methylphenyl)-3-nitrosoimidazo[1,2-a]pyridine
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: AWLZFZQWMQSKLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-甲基-2-(4-甲基苯基)咪唑[1,2-a]吡啶 在 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以85%的产率得到6-methyl-3-nitroso-2-(p-tolyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Catalyst-Free Regioselective C-3 Nitrosation of Imidazopyridines with tert-Butyl Nitrite under Neutral Conditions

  摘要：

  We have successfully developed a novel and efficient catalyst-free method for the synthesis of 3-nitroso-substituted imidazopyridines, from readily available imidazo[1,2-a]pyridines and tert-butyl nitrite, in good to excellent yields. Importantly, the use of transition-metal catalysts, stoichiometric amounts of acids, and toxic or potentially dangerous oxidants is avoided. This easy and practical method complements nitrosation reactions by expanding the scope and practicality, and should attract much attention in synthetic and pharmaceutical chemistry.

  DOI：

  10.1055/s-0035-1560508

文献信息

• NaNO₂/I₂-Mediated Regioselective Synthesis of Nitrosoimidazoheterocycles from Acetophenones by a Domino Process
  作者：Sushobhan Mukhopadhyay、Shashikant U. Dighe、Shivalinga Kolle、Praveen K. Shukla、Sanjay Batra

  DOI：10.1002/ejoc.201600553

  日期：2016.8

  regioselective synthesis of nitrosoimidazoheterocycles from the reaction of 2-aminopyridines and acetophenones in the presence of NaNO2 and I2 is described. The reaction is suggested to proceed by a domino process involving sequential imine formation, iodination, iodide displacement by the nitro group, and finally intramolecular cyclization. Reaction of these 3-nitrosoimidazo[1,2-a]pyridines with aldehydes

  描述了在 NaNO2 和 I2 存在下，2-氨基吡啶和苯乙酮反应的亚硝基咪唑杂环的区域选择性合成。建议该反应通过多米诺过程进行，包括依次形成亚胺、碘化、硝基取代碘，最后进行分子内环化。这些 3-亚硝基咪唑并 [1,2-a] 吡啶与醛在 Fe/AcOH 存在下的反应通过还原提供 5-取代的吡啶并 [2',1':2,3] 咪唑并 [4,5-c] 异喹啉亚硝基，然后在一锅中进行 Pictet-Spengler 反应。评估合成的化合物的抗菌和抗真菌活性。
• Catalyst-Free Regioselective C-3 Nitrosation of Imidazopyridines with tert-Butyl Nitrite under Neutral Conditions
  作者：Hua Wang、Daoshan Yang、Kelu Yan、Wei Wei、Yao Liu、Mengqi Zhang、Caixia Zhao、Laijin Tian

  DOI：10.1055/s-0035-1560508

  日期：——

  We have successfully developed a novel and efficient catalyst-free method for the synthesis of 3-nitroso-substituted imidazopyridines, from readily available imidazo[1,2-a]pyridines and tert-butyl nitrite, in good to excellent yields. Importantly, the use of transition-metal catalysts, stoichiometric amounts of acids, and toxic or potentially dangerous oxidants is avoided. This easy and practical method complements nitrosation reactions by expanding the scope and practicality, and should attract much attention in synthetic and pharmaceutical chemistry.