ethyl 2-(2-phenyl-imidazo[1,2-a]pyridin-3-ylamino)acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(2-phenyl-imidazo[1,2-a]pyridin-3-ylamino)acetate
• 英文别名: Ethyl 2-[(2-phenylimidazo[1,2-a]pyridin-3-yl)amino]acetate
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: WMAPFMLTDHPAMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 异氰基乙酸乙酯 、 苯甲醛 在 1-butylsulfonic-3-methylimidazolium trifluoromethanesulfonate 作用下， 以 乙醇 为溶剂， 以83%的产率得到ethyl 2-(2-phenyl-imidazo[1,2-a]pyridin-3-ylamino)acetate
  参考文献：
  名称：

  可重复使用的 Brønsted-酸性离子液体催化的 Groebke-Blackburn-Bienaymé 多组分反应

  摘要：

  Brønsted 酸性离子液体可有效催化 Groebke-Blackburn-Bienaymé 多组分反应合成咪唑并[1,2- a ]吡啶和咪唑并[ 2,1- b ]噻唑，产率适中（42-93%） ，在热或微波加热下。均相酸性催化剂可以在四个连续的反应循环中回收和重复使用。

  DOI：

  10.1002/ejoc.202200615

文献信息

• Introducing ferrocene into imidazo[1,2- a ]pyridine by Groebke three-component-reaction for scavenging radicals and inhibiting DNA oxidation
  作者：Gao-Lei Xi、Zai-Qun Liu

  DOI：10.1016/j.tet.2015.10.080

  日期：2015.12

  With 2-aminopyridine or quinoline, seven aldehydes, and five isocyanides as reactants, sixteen imidazo [1,2-a]pyridines or quinolines were synthesized by using Groebke three-component-reaction (3CR). The radical-scavenging ability was evaluated by quenching 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+.)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radicals, respectively. Compounds consisting of double ferrocenyl groups coupled with quinoline and ester moieties showed good potencies for scavenging ABTS(+.) and DPPH, while phenolic hydroxyl groups activated the corresponding imidazo[1,2-a]pyridines to react with galvinoxyl radical. Moreover, the oxidation of DNA was caused by 2,2'-azobis(2-amidinopropane hydrochloride) (MPH), and all of the synthetic compoundS were found to inhibit the DNA oxidation. Especially, the scaffold of imidazo[1,2-a]pyridine exhibited antioxidative effect on the DNA oxidation, while the most active compound was ascribed to double ferrocenyl groups incorporating with imidazo[1,2-a]quinoline. The present results showcased that the ferrocenyl group attaching to the scaffold of imidazo[1,2-a]pyridine or quinoline was beneficial for the antioxidative effect. (C) 2015 Elsevier Ltd. All rights reserved.
• Groebke‐Blackburn‐Bienaymé Multicomponent Reaction Catalysed by Reusable Brønsted‐Acidic Ionic Liquids
  作者：Nicolas S. Anjos、Agáta I. Chapina、Ana R. Santos、Peter Licence、Luiz S. Longo

  DOI：10.1002/ejoc.202200615

  日期：2022.10.26

  Groebke-Blackburn-Bienaymé multicomponent reactions can be efficiently catalysed by Brønsted acidic ionic liquids for the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles in moderate to excellent yields (42–93 %), either under thermal or microwave heating. The homogeneous acidic catalyst can be recycled and reused in four consecutive reaction cycles.

  Brønsted 酸性离子液体可有效催化 Groebke-Blackburn-Bienaymé 多组分反应合成咪唑并[1,2- a ]吡啶和咪唑并[ 2,1- b ]噻唑，产率适中（42-93%） ，在热或微波加热下。均相酸性催化剂可以在四个连续的反应循环中回收和重复使用。