2-phenyl-3-(pyridin-4-yl)imidazo[1,2-a]pyridine | 1353511-55-3

• 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-phenyl-3-(pyridin-4-yl)imidazo[1,2-a]pyridine
• 英文别名: 2-Phenyl-3-pyridin-4-ylimidazo[1,2-a]pyridine；2-phenyl-3-pyridin-4-ylimidazo[1,2-a]pyridine
• CAS: 1353511-55-3
• 化学式: C₁₈H₁₃N₃
• 分子量: 271.321
• InChiKey: PCJHEHKOLTYNST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯咪唑并[1,2-A]吡啶 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 2-phenyl-3-(pyridin-4-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  一个有效的访问2,3- diarylimidazo [1,2一]吡啶经由咪唑并[1,2一]吡啶-2-基三氟甲磺酸酯通过Suzuki交叉偶联反应直接芳基化序列

  摘要：

  描述了一种制备2,3-二芳基咪唑并[1,2- a ]吡啶的有效方法。该过程涉及Suzuki交叉偶联反应，然后在3位直接芳基化。咪唑并[1,2- a ]吡啶-2-基三氟甲磺酸酯被确定为合适的偶联伴侣，从而可以使用各种高度官能化的2， 3-二芳基咪唑并[1,2- a ]吡啶。

  DOI：

  10.1016/j.tetlet.2011.11.015

文献信息

• Efficient Access to 2,3-Diarylimidazo[1,2-<i>a</i>]pyridines via a One-Pot, Ligand-Free, Palladium-Catalyzed Three-Component Reaction under Microwave Irradiation
  作者：Yuanxiang Wang、Brendan Frett、Hong-yu Li

  DOI：10.1021/ol501136e

  日期：2014.6.6

  ligand-free, Pd(OAc)2-catalyzed, three-component reaction for the synthesis of 2,3-diarylimidazo[1,2-a]pyridines was developed under microwave irradiation. With the high availability of commercial reagents and great efficiency in expanding molecule diversity, this methodology is superior to the existing procedures for the synthesis of 2,3-diarylimidazo[1,2-a]pyridines analogues.

  在微波辐射下，开发了一种快速的单锅、无配体、Pd(OAc) 2催化的三组分反应，用于合成 2,3-二芳基咪唑并[1,2- a ]吡啶。由于商业试剂的高可用性和扩展分子多样性的高效率，该方法优于现有的合成 2,3-二芳基咪唑并[1,2- a ]吡啶类似物的方法。
• An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via imidazo[1,2-a]pyridin-2-yl triflate through a Suzuki cross-coupling reaction-direct arylation sequence
  作者：Sophie Marhadour、Marc-Antoine Bazin、Pascal Marchand

  DOI：10.1016/j.tetlet.2011.11.015

  日期：2012.1

  An efficient method to prepare 2,3-diarylimidazo[1,2-a]pyridines is described. The procedure involves a Suzuki cross-coupling reaction followed by a direct arylation at position 3. Imidazo[1,2-a]pyridin-2-yl triflate was identified as a suitable coupling partner, permitting access to a variety of highly functionalized 2,3-diarylimidazo[1,2-a]pyridines.

  描述了一种制备2,3-二芳基咪唑并[1,2- a ]吡啶的有效方法。该过程涉及Suzuki交叉偶联反应，然后在3位直接芳基化。咪唑并[1,2- a ]吡啶-2-基三氟甲磺酸酯被确定为合适的偶联伴侣，从而可以使用各种高度官能化的2， 3-二芳基咪唑并[1,2- a ]吡啶。
• An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via silver(I)-catalyzed C-H bond functionalization
  作者：Mehdi Khoshneviszadeh、Mehdi Soheilizad、Maryam Fardpour、Mohammad Mahdavi

  DOI：10.1007/s00706-017-1950-8

  日期：2017.10

  AbstractAn efficient and economic Ag-catalyzed method for the direct cross-coupling of unactivated imidazo[1,2-a]pyridines with arylboronic acids has been developed. This approach leads to the formation of corresponding 2,3-diarylimidazo[1,2-a]pyridine derivatives as biological and pharmaceutical materials of interest in good yields under mild reaction conditions. Graphical abstract

  摘要已开发出一种有效且经济的Ag催化方法，用于将未活化的咪唑并[1,2- a ]吡啶与芳基硼酸直接交叉偶联。该方法导致在温和的反应条件下以高收率形成相应的2,3-二芳基咪唑并[1,2- a ]吡啶衍生物，作为感兴趣的生物和制药材料。 图形概要
• Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents
  作者：Sophie Marhadour、Pascal Marchand、Fabrice Pagniez、Marc-Antoine Bazin、Carine Picot、Olivier Lozach、Sandrine Ruchaud、Maud Antoine、Laurent Meijer、Najma Rachidi、Patrice Le Pape

  DOI：10.1016/j.ejmech.2012.10.048

  日期：2012.12

  A novel series of 2,3-diarylimidazo[1,2-a]pyridines was synthesized and evaluated for their antileishmanial activities. Four derivatives exhibited good activity against the promastigote and intracellular amastigote stages of Leishmania major, coupled with a low cytotoxicity against the HeLa human cell line. The impact of compound lipophilicity on antiparasitic activities was investigated by Log D comparison. Although LmCK1 could be the parasitic target for three compounds (13, 18, 21), the inhibition of another target is under study to explain the antileishmanial effect of the most promising compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki–Miyaura and Sonogashira cross-coupling reactions
  作者：P.-O. Delaye、M. Pénichon、H. Allouchi、C. Enguehard-Gueiffier、A. Gueiffier

  DOI：10.1039/c7ob00624a

  日期：——

  allowed the selective introduction of aryl, heteroaryl, alkyl and alkynyl substituents at both 2- and 3-positions, by using Suzuki–Miyaura and Sonogashira cross-coupling reactions. A library of compounds diversely substituted on 2- and 3-positions can be easily prepared from a common, stable and easily accessible starting material.

  建立了一种有效的2,3-二卤代咪唑并[1,2- a ]吡啶区域控制功能化方法。通过使用Suzuki-Miyaura和Sonogashira交叉偶联反应，该序列允许在2位和3位选择性引入芳基，杂芳基，烷基和炔基取代基。可以轻松地从一种常见，稳定且易于获取的起始原料制备在2位和3位上不同取代的化合物库。