4-(2-phenylimidazo[1,2-a]pyridin-3-yl)benzonitrile | 1416319-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-phenylimidazo[1,2-a]pyridin-3-yl)benzonitrile
• 英文别名: 4-(2-Phenylimidazo[1,2-a]pyridin-3-yl)benzonitrile
• CAS: 1416319-53-3
• 化学式: C₂₀H₁₃N₃
• 分子量: 295.343
• InChiKey: JLVGQDKKCXWUGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-phenylimidazo[1,2-a]pyridin-3-yl)benzonitrile 在 双氧水 、 potassium carbonate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以66%的产率得到4-(2-Phenylimidazo[1,2-a]pyridin-3-yl)benzamide
  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
• 作为产物：
  描述：

  imidazo[1,2-a]pyridin-2-yl trifluoromethanesulfonate 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 43.0h， 生成 4-(2-phenylimidazo[1,2-a]pyridin-3-yl)benzonitrile
  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

• Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
  作者：Bao-Tian Luo、Huan Liu、Zhi-Jie Lin、Jingxing Jiang、Dong-Sheng Shen、Rui-Zhi Liu、Zhuofeng Ke、Feng-Shou Liu

  DOI：10.1021/acs.organomet.5b00181

  日期：2015.10.26

  In the present work, a series of alpha-hydroxyimine palladium complexes with bulky substituents (i.e., [Ar-N=C(R)-C(R)(2)-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylinethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.