4,5-diphenyl-2-(1,3-diphenyl-1H-pyrazol-4-yl)-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-diphenyl-2-(1,3-diphenyl-1H-pyrazol-4-yl)-1H-imidazole
• 英文别名: 4-(4,5-diphenyl-1H-imidazol-2-yl)-1,3-diphenyl-1H-pyrazole；1,3-diphenyl-4-(4,5-diphenyl-1H-imidazol-2-yl)-1H-pyrazole；4-(4,5-diphenyl-1H-imidazole-2-yl)-1,3-diphenyl-1H-pyrazole；2-(1,3-diphenylpyrazol-4-yl)-4,5-diphenyl-1H-imidazole
• 化学式: C₃₀H₂₂N₄
• 分子量: 438.531
• InChiKey: SRUGWLZRNSAQHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-2-(1-苯基亚乙基)肼 在 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 生成 4,5-diphenyl-2-(1,3-diphenyl-1H-pyrazol-4-yl)-1H-imidazole
  参考文献：
  名称：

  Synthesis, Characterization and Biological Screening of Novel Imidazolylpyrazole Scaffolds

  摘要：

  一系列新的3-(4-芳基)-4-(4,5-二苯基-1H-咪唑-2-基)-1-苯基-1H-吡唑酮化合物被合成，采用了著名的Debus-Radziszewski反应。所有新合成化合物的结构均经过了各种光谱技术的表征，包括傅里叶变换红外光谱、1H和13C核磁共振、液相质谱和元素分析。所有这些化合物也被筛选用于抗菌活性，对金黄色葡萄球菌、肺炎克雷伯菌和黑曲霉和红色念珠菌的真菌菌株进行了筛选。

  DOI：

  10.14233/ajchem.2022.23570

文献信息

• An expedient one-pot synthesis of highly substituted imidazoles using supported ionic liquid-like phase (SILLP) as a green and efficient catalyst and evaluation of their anti-microbial activity
  作者：Maryam Saffari Jourshari、Manouchehr Mamaghani、Farhad Shirini、Khalil Tabatabaeian、Mehdi Rassa、Hadiss Langari

  DOI：10.1016/j.cclet.2013.06.005

  日期：2013.11

  An efficient method for the synthesis of imidazole derivatives by a three-component condensation of benzil or 9,10-phenanthrenequinone, aldehydes and ammonium acetate using supported ionic liquid-like phase (SILLP) catalyst under ultrasonic irradiation or classical heating conditions is reported. The present methodology offers several advantages, such as excellent yields, simple procedures, short reaction

  据报道，在超声辐射或经典加热条件下，使用负载型离子液体相（SILLP）催化剂通过苯甲醚或9,10-菲醌，醛和乙酸铵的三组分缩合合成咪唑衍生物的有效方法。本方法学具有几个优点，例如优异的产率，简单的方法，短的反应时间，简单的后处理和温和的条件。催化剂易于通过过滤从产物中分离出来，并且还表现出显着的可重复使用的活性。还评估了这些高度取代的咪唑的抗微生物活性。
• Ionic Liquid: An Efficient and Facile Catalyst for the Synthesis of Trisubstituted Imidazole Derivatives via Multi-Component Pathway Using Green Techniques
  作者：Gopinath D. Shirole、Sharad N. Shelke

  DOI：10.2174/1570178614666161114165113

  日期：2017.1.3

  Background: A green path for the synthesis of 3-aryl-1-phenyl-4-(4,5-diphenyl-1H-imidazol-2-yl)-1Hpyrazole derivatives using [BMIM][BF4] as a catalyst and green methods such as ultrasound and microwave irradiation is discussed in this paper. The titled compounds were obtained by the multi-component condensation of various 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehydes, benzil and ammonium acetate. One pot synthesis, simple reaction conditions and quantitative yields illustrate the utility of this green approach. Methods: Conventional Reflux Condition: A mixture of 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM][BF4] (15 mmol %) was placed in a round bottom flask containing 10 mL of ethanol. The reaction mixture was refluxed for completion. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured over crushed ice. Solid imidazole thus obtained was separated by filtration, dried well, and recrystallized by ethanol. Ultrasound Irradiation Method: A mixture of 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM][BF4] (15 mmol %) was placed in a round bottom flask containing 10 mL of ethanol. The round bottom flask was placed in an US bath at 50ºC for 80-90 min. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured into crushed ice, solid imidazoles thus obtained were separated by filtration, dried well, and recrystallized by ethanol. Microwave Irradiation Method: A 10 mL round bottom flask was charged with 3-aryl-1-phenyl- 1H-pyrazole-4-carboxaldehyde 1 (1 mmol), benzil 2 (1 mmol), ammonium acetate 3 (2 mmol) and catalytic amount of [BMIM] [BF4] (15 mmol %), and placed under MW irradiation at 240 watts for 7-9 min. The course of the reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was poured over crushed ice, the solid imidazole thus obtained was separated by filtration, dried well, and recrystallized by ethanol. Results: The 3-aryl-1-phenyl-4-(4,5-diphenyl-1H-imidazol-2-yl)-1H-pyrazole derivatives 4a-i (Scheme 1, Table 2) were synthesized by using [BMIM] [BF4] as a catalyst with good yields under reflux in ethanol (68-70%), US irradiation in ethanol (76-80%) and MW irradiation (80-86%) without solvent. All these methods provided good results with IL [BMIM][BF4]. However, the MW and US irradiation methods give good yield in a short period of time with 3-aryl-1-phenyl-1H-pyrazole-4-carboxaldehyde 1 containing a variety of substituents, whereas the conventional reflux condition gives lower yields and takes longer time as compared with MW and US irradiation. The structures of the synthesized compounds have been confirmed on the basis of spectroscopic techniques such as FTIR, HRMS, LCMS, 1H and 13C NMR. Conclusion: In conclusion, we have synthesized differently substituted imidazoles using [BMIM][BF4] as a catalyst under MW and US irradiation via MC condensation strategy. Under the conventional reflux conditions, we get a lower yield in a longer time, while US and MW assisted synthesis gave better results. Comparatively IL [BMIM][BF4] with US and MW irradiation protocol provides several advantages such as improved reaction speed, shorter reaction times, superior yields and a significant contribution towards sustainability.

  背景：本文讨论了使用[BMIM][BF4]作为催化剂，以及超声波和微波辐射等绿色方法合成3-芳基-1-苯基-4-(4,5-二苯基-1H-咪唑-2-基)-1H-吡唑衍生物的绿色途径。所述化合物通过各种3-芳基-1-苯基-1H-吡唑-4-醛、苯基和醋酸铵的多组分缩合获得。一锅合成、简单的反应条件和定量产率展示了这种绿色方法的实用性。 方法：常规回流条件：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM][BF4]（15 mmol%）混合，放入含10 mL乙醇的圆底烧瓶中。反应混合物回流至反应完成。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中。通过过滤分离得到的固体咪唑，充分干燥，并用乙醇重结晶。 超声辐射法：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM][BF4]（15 mmol%）混合，放入含10 mL乙醇的圆底烧瓶中。圆底烧瓶放入50ºC的超声波浴中80-90分钟。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中，分离得到的固体咪唑，通过过滤、充分干燥并用乙醇重结晶。 微波辐射法：将3-芳基-1-苯基-1H-吡唑-4-醛1（1 mmol）、苯基2（1 mmol）、醋酸铵3（2 mmol）和催化量的[BMIM] [BF4]（15 mmol%）放入10 mL的圆底烧瓶中，在240瓦的微波辐射下加热7-9分钟。通过薄层色谱监测反应进程。反应完成后，将混合物倒入碎冰中，分离得到的固体咪唑，通过过滤、充分干燥并用乙醇重结晶。 结果：使用[BMIM][BF4]作为催化剂，在乙醇回流（68-70%）、乙醇的超声波照射（76-80%）和微波照射（80-86%）下以良好的产率合成了3-芳基-1-苯基-4-(4,5-二苯基-1H-咪唑-2-基)-1H-吡唑衍生物4a-i（方案1，表2）。所有这些方法在使用IL [BMIM][BF4]时都取得了良好的结果。然而，微波和超声波辐射法在短时间内给予了良好的产率，同样的反应所用的3-芳基-1-苯基-1H-吡唑-4-醛1含有多种取代基，而传统回流条件给出的产率较低且时间较长。合成化合物的结构通过FTIR、HRMS、LCMS、1H和13C NMR等光谱技术得到确认。 结论：总之，我们采用[BMIM][BF4]作为催化剂，通过微波和超声辐射合成了不同取代基的咪唑，采用MC缩合策略。在常规回流条件下，我们获得较低的产率所需的时间较长，而超声和微波辅助合成则取得了更好的结果。比较而言，使用[BMIM][BF4]与超声和微波辐射方案提供了多种优势，如提高反应速度、缩短反应时间、优越的产率以及对可持续性的显著贡献。
• Synthesis, Characterization, and Biological Evaluation of Some Tri-Substituted Imidazole/thiazole Derivatives
  作者：H. B'Bhatt、S. Sharma

  DOI：10.1002/jhet.1992

  日期：2015.7

  spectral analysis (FTIR, 1H and 13C FT NMR, and LC–MS). All the compounds were screened for their antibacterial, antifungal, and antimycobacterial activities. Antimicrobial activity was evaluated against some bacterial strains such as Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442), and the H37Rv strain of Mycobacterium tuberculosis

  通过Radziszewski反应制备了一系列新颖的三取代的咪唑/噻唑衍生物化合物（3a，3b，3c，3d，3e，3f，3g，3h，3i）。苯甲（1），乙酸铵或硫氰酸铵和1-苯基-3-（对位取代苯基）-1 H-吡唑-4-甲醛（2a，2b，2c，2d，2e，2f，2g）反应得到所需产物。通过元素分析（CHNS）和光谱分析（FTIR，1 H和13 C FT NMR和LC-MS）对合成的化合物进行表征。筛选所有化合物的抗菌，抗真菌和抗分枝杆菌活性。评估了对某些细菌菌株的抗菌活性，例如大肠杆菌（MTCC 443），铜绿假单胞菌（MTCC 1688），金黄色葡萄球菌（MTCC 96），化脓性链球菌（MTCC 442）和结核分枝杆菌H 37 Rv菌株，以及观察到了针对白色念珠菌等菌株的真菌活性（MTCC 227），黑曲霉（MTCC 282）和黑曲霉（MTCC 1323）。发现所有合成的化合物对上述所选菌株均具有中等至优异的活性。
• Synthesis, Characterization and Biological Screening of Novel Imidazolylpyrazole Scaffolds
  作者：JYOTSNA SHARMA、HARDEEP SINGH TULI、MAYANK KINGER、RAM PAL、ZAHOOR ABBAS、MANOJ KUMAR

  DOI：10.14233/ajchem.2022.23570

  日期：——

  A novel series of 3-(4-aryl)-4-(4,5-diphenyl-1H-imidazol-2-yl)-1-phenyl-1H-pyrazole was synthesized by employing the well-known Debus-Radziszewski reaction. Structures of all the newly synthesized compounds have been characterized by various spectroscopic techniques viz. FTIR, 1H and 13C NMR, LC-MS and elemental analysis. All these compounds were also screened for antimicrobial potential against bacterial strains of S. aureus, K. pneumoniae and fungal strains of A. niger and T. rubrum.

  一系列新的3-(4-芳基)-4-(4,5-二苯基-1H-咪唑-2-基)-1-苯基-1H-吡唑酮化合物被合成，采用了著名的Debus-Radziszewski反应。所有新合成化合物的结构均经过了各种光谱技术的表征，包括傅里叶变换红外光谱、1H和13C核磁共振、液相质谱和元素分析。所有这些化合物也被筛选用于抗菌活性，对金黄色葡萄球菌、肺炎克雷伯菌和黑曲霉和红色念珠菌的真菌菌株进行了筛选。