2-(3,5-dichlorophenyl)-3-phenylimidazo[1,2-a]pyridine | 1353511-69-9

• 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-(3,5-dichlorophenyl)-3-phenylimidazo[1,2-a]pyridine
• 英文别名: 2-(3,5-Dichlorophenyl)-3-phenylimidazo[1,2-a]pyridine
• CAS: 1353511-69-9
• 化学式: C₁₉H₁₂Cl₂N₂
• 分子量: 339.224
• InChiKey: KLQRTUVTMPDMMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 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：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,5-二氯苯硼酸 在 四(三苯基膦)钯 、 tricyclohexylphosphine tetrafluoroborate 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 三甲基丙酮酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 18.75h， 生成 2-(3,5-dichlorophenyl)-3-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-diarylimidazo[1,2-a]pyridines as antileishmanial agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.10.048

文献信息

• 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。
• Halogen Bond-Activated Visible-Light-Mediated Regioselective C–H Arylation of 2-Phenylimidazo-[1,2-<i>a</i>]pyridines
  作者：Imran Kazi、Anuradha Nandy、Raji Selvam、Govindasamy Sekar

  DOI：10.1021/acs.joc.2c01548

  日期：2022.9.16

  An efficient method for transition metal-free halogen bond-assisted regioselective C–H arylation of 2-phenylimidazo-[1,2-a]pyridines under visible-light condition has been developed. The halogen bond between an aryl halide and base KOtBu initiates an electron transfer process and generates an aryl radical, which catalyzes its coupling with 2-phenylimidazo-[1,2-a]pyridines to give arylated products

  开发了一种在可见光条件下无过渡金属卤素键辅助区域选择性 C-H 芳基化 2-苯基咪唑-[1,2- a ]吡啶的有效方法。芳基卤化物和碱基 KO t Bu之间的卤素键引发电子转移过程并产生芳基自由基，其催化其与 2-苯基咪唑-[1,2- a ] 吡啶偶联以高收率得到芳基化产物。一些对照实验、密度泛函理论计算和紫外-可见分析表明芳基卤化物和 KO t Bu 之间存在卤素键。该方法已成功用于合成抗寄生虫剂。