2-(2,4-dichlorophenyl)-3-methylimidazo[1,2-a]pyridine | 1426080-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,4-dichlorophenyl)-3-methylimidazo[1,2-a]pyridine
• CAS: 1426080-01-4
• 化学式: C₁₄H₁₀Cl₂N₂
• 分子量: 277.153
• InChiKey: MXOVMLWFQONKHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 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：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 (E)-2,4-dichloro-1-(2-nitroprop-1-en-1-yl)benzene 在 iron(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以76%的产率得到2-(2,4-dichlorophenyl)-3-methylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Iron(II)-Catalyzed Denitration Reaction: Synthesis of 3-Methyl-2-arylimidazo[1,2-a]pyridine Derivatives from Aminopyridines and 2-Methylnitroolefins

  摘要：

  A variety of ways to synthesize imidazo[1,2-a]pyridines have been reported and many approaches are devoted to the functionalization of imidazo[1,2-a]pyridines. However, the use of a denitration reaction in the synthesis of imidazo[1,2-a]pyridines has not been reported. We report here the iron-catalyzed synthesis of 3-methyl-2-arylimidazo [1,2-a] pyridine derivatives from aminopyridines and 2-methyl-nitroolefins. The procedure, using FeCl2 as catalyst, is simple and inexpensive. Various functional groups are tolerated and provide the products in good yields.

  DOI：

  10.1055/s-0032-1317685

文献信息

• Iron(III)-Catalyzed Denitration Reaction: One-Pot Three-Component Synthesis of Imidazo[1,2-<i>a</i>]pyridine Derivatives
  作者：Hao Yan、Yuling Wang、Congming Pan、Hao Zhang、Sizhuo Yang、Xiaoyu Ren、Jian Li、Guosheng Huang

  DOI：10.1002/ejoc.201301658

  日期：2014.5

  An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes and nitroalkanes, straightforwardly forms imidazo[1,2-a]pyridine derivatives and is described in this report. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields.

  铁 (III) 催化的 2-氨基吡啶、醛和硝基烷烃的一锅三组分交叉偶联硝化反应直接形成咪唑并 [1,2-a] 吡啶衍生物，并在本报告中进行了描述。该系统显示出良好的官能团耐受性，并以中等至良好的产率顺利进行。
• [EN] SELECTIVE LIGANDS OF HUMAN CONSTITUTIVE ANDROSTANE RECEPTOR<br/>[FR] LIGANDS SÉLECTIFS DU RÉCEPTEUR D'ANDROSTANE CONSTITUTIF HUMAIN
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR V V I

  公开号：WO2020221380A1

  公开（公告）日：2020-11-05

  The present invention provides a structurally novel class of heterocyclic compounds of general formula I wherein L1 is heteroaryl and L2 is heteroaryl or aryl. The novel compounds are useful in a method of prevention or treatment of a condition which is mediated by the action, or by loss of action, of Constitutive androstane receptor (CAR) receptor or its endogenous ligands. The present invention thus provides the novel compounds for medicinal use, as well as pharmaceutical composition containing said compounds. (I)

  本发明提供了一类结构新颖的杂环化合物，其通用公式为I，其中L1是杂芳基，L2是杂芳基或芳基。这些新颖化合物在预防或治疗由构成雄烷受体（CAR）受体或其内源性配体的作用或作用丧失介导的疾病的方法中是有用的。因此，本发明提供了用于药用的新颖化合物，以及含有所述化合物的药物组合物。(I)
• Polyethylene Gylcol (PEG-400) as an Efficient and Recyclable Reaction Medium for One-Pot Three-Component Synthesis of Imidazo[1,2-a]pyridine Derivatives
  作者：P. Ramesh、K. Bhaskar

  DOI：10.14233/ajchem.2016.20061

  日期：——

  Polyethylene glycol (PEG) was found to be an inexpensive nontoxic and effective medium for the one-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives under catalyst-free conditions in excellent yields. Environmental acceptability, low cost, high yields and recyclability of the polyethylene glycol are the important features of this protocol.

  研究发现，聚乙二醇（PEG）是一种廉价、无毒且有效的介质，可在无催化剂条件下单锅三组分合成咪唑并[1,2-a]吡啶衍生物，且收率极高。环境可接受性、低成本、高产率以及聚乙二醇的可回收性是该方案的重要特点。