2-methyl-1-(4-nitrophenyl)-1H-benzoimidazole | 77246-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-methyl-1-(4-nitrophenyl)-1H-benzoimidazole
• 英文别名: 2-methyl-1-(4-nitrophenyl)-1H-benzo[d]imidazole；2-Methyl-1-(4-nitrophenyl)benzimidazole
• CAS: 77246-15-2
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: FKAKCQMIWJTHBV-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C(Solv: benzene (71-43-2))
• 沸点：
  461.6±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(2-(4-nitrophenylamino)phenyl)ethanone oxime 在 三乙胺 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 以77%的产率得到2-methyl-1-(4-nitrophenyl)-1H-benzoimidazole
  参考文献：
  名称：

  Synthesis of N-Arylindazoles and Benzimidazoles from a Common Intermediate

  摘要：

  A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals

  DOI：

  10.1021/ol101899q

文献信息

• N-Arylations of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides Using a Copper(I) Oxide Nanoparticle/1,10-Phenanthroline Catalytic System
  作者：Jin-Heng Li、Bo-Xiao Tang、Sheng-Mei Guo、Man-Bo Zhang

  DOI：10.1055/s-2008-1067014

  日期：2008.6

  and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu 2 O) nanoparticles is demonstrated. Four types of Cu 2 O were evaluated: the bulky compound and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu 2 O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu 2 O nanoparticles

  演示了含氮杂环（即咪唑、三唑和吲哚）的无溶剂 N-芳基化的一般程序，其中芳基和杂芳基卤化物由氧化铜 (I) (Cu 2 O) 纳米颗粒催化。评估了四种类型的 Cu 2 O：大体积化合物及其立方、八面体和球形纳米颗粒形式。结果表明，Cu 2 O 纳米颗粒，特别是立方形式，对 N-芳基化反应非常有效。在立方 Cu 2 O 纳米粒子、1,10-菲咯啉和四丁基氟化铵存在下，多种含氮杂环在 110-145 °C 下与芳基和杂芳基卤化物顺利进行 N-芳基化反应，得到相应的产物以优异的产量。值得注意的是，该反应是在无溶剂条件下进行的。
• <scp> <i>N</i> ‐Heterocyclic </scp> Carbene Copper(I) Complex Catalyzed Coupling of (Hetero)aryl Chlorides and Nitrogen Heterocycles: Highly Efficient Catalytic System
  作者：Mengyao Zhang、Yingying Zhang、Huixin Zhang、Yongfei Zeng、Guiyan Liu

  DOI：10.1002/cjoc.201900461

  日期：2020.11

  A highly efficient catalytic system for the N‐arylation reactions of (hetero)aryl chlorides and nitrogen heterocycles with a copper(I) complex containing a 1,10‐phenanthroline analogue N‐heterocyclic carbene (NHC) has been reported. The complex was characterized by 1H NMR and 13C NMR spectroscopy and elemental analysis, and its structure was determined by single‐crystal X‐ray diffraction. The NHC‐copper(I)

  已经报道了一种高效的催化体系，用于（杂）芳基氯和氮杂环与含1,10-菲咯啉类似物N-杂环卡宾（NHC）的铜（I）配合物的N-芳基化反应。该复合物通过1 H NMR和13 C NMR光谱学和元素分析进行表征，并通过单晶X射线衍射确定其结构。NHC-铜（I）络合物被用作（杂）芳基氯与各种唑类的Ullmann型N-芳基化反应的前催化剂。各种受阻和官能化的吡咯和（杂）芳基氯化物均以良好的转化率获得了优异的收率。
• <i>N</i>,<i>N</i>′-(Phenylmethylene)diacetamide Analogues as Economical and Efficient Ligands in Copper-Catalyzed Arylation of Aromatic Nitrogen-Containing Heterocycles
  作者：Yuan-Jiang Pan、Jie-Ping Wan、Yun-Feng Chai、Jian-Mei Wu

  DOI：10.1055/s-0028-1087350

  日期：2008.12

  N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields.

  N,N′-(苯亚甲基)二乙酰胺类似物是通过醛与酰胺或尿素的缩合反应简单制备而成的，发现其在铜催化的芳基卤化物与各种杂环核苷酸的偶联反应中是有效的配体。新开发的配体在该转化过程中显示了广泛的应用范围。包括咪唑、苯并咪唑、呋喃、吲哚和苯并三唑等化合物成功地与多样化的芳香卤化物发生芳基化反应，得到相应的产物，产率中等到优秀。
• Metal-Free One-Pot Synthesis of<i>N</i>,<i>N′</i>-Diarylamidines and<i>N</i>-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines
  作者：So Won Youn、Eun Mi Lee

  DOI：10.1021/acs.orglett.6b02994

  日期：2016.11.4

  efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N′-diarylamidines from arenediazonium salts, nitriles, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive

  已经开发了一种高效且简便的无金属单锅反应，可通过化学方法从槟榔二唑鎓盐，腈和游离苯胺中原位生成N，N'-二芳基idine胺，从而提供不同取代的N-芳基苯并咪唑。该协议的优点包括：在无金属和温和条件下操作简单，操作简单的一锅法；直接使用廉价和可商购的化学药品；因此，具有成本效益且更环保。
• Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
  作者：Zhen-Hua Li、Xiao-Meng Sun、Jin-Jing Qin、Zhi-Yong Tan、Wen-Biao Wang、Yao Ma

  DOI：10.1016/j.tet.2020.130945

  日期：2020.2

  An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N-N and N-C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope. (C) 2020 Elsevier Ltd. All rights reserved.