methyl 3-(2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: WUXOBLLSKVSBRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(乙酰氨基)-1-苯乙烯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 氧气 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 生成 methyl 3-(2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate
  参考文献：
  名称：

  Copper-Mediated Aerobic Oxidative Synthesis of 3-Bromo-imidazo[1,2-a]pyridines with Pyridines and Enamides

  摘要：

  A conversion of pyridines and enamides for the synthesis of 3-bromo-imidazo[1,2-c]pyridines was developed by copper-mediated aerobic oxidative coupling in a one-pot manner. This procedure tolerates various functional groups and affords a series of 3-bromo-imidazo[1,2-c]pyridines under mild conditions.

  DOI：

  10.1021/acs.joc.5b02384

文献信息

• K2S2O8-Mediated halogenation of 2-arylimidazo[1,2-a]pyridines using sodium halides as the halogen sources
  作者：Praewpan Katrun、Chutima Kuhakarn

  DOI：10.1016/j.tetlet.2019.03.008

  日期：2019.4

  halogenation of 2-arylimidazo[1,2-a]pyridines using sodium chloride/bromide/iodide as the halogen sources in the presence of K2S2O8 as an easy-to-handle oxidizing agent was developed. The present work offers an efficient and rapid access to 3-chloro-, 3-bromo- and 3-iodo-2-arylimidazo[1,2-a]pyridines which can be readily converted to C3-substituted imidazo[1,2-a]pyridines by cross-coupling reactions.

  开发了在K 2 S 2 O 8作为易于处理的氧化剂存在下，使用氯化钠/溴化物/碘化物作为卤素源，方便地卤化2-芳基咪唑并[1,2- a ]吡啶的方法。本工作提供了一种快速有效地获得3-氯-，3-溴-和3-碘-2-芳基咪唑并[1,2- a ]吡啶的方法，这些吡啶基很容易转化为C 3取代的咪唑并[1,2] -一个]吡啶通过交叉偶联反应。
• Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide
  作者：Qing-Wen Gui、Hongmei Jiang、Dingyi Guo、Yixin Zhang、Qin-Peng Shen、Shiyun Tang、Junheng You、Yi Huo、Huixian Wang

  DOI：10.1055/s-0040-1707856

  日期：2020.9

  Abstract By using pyridinium tribromide as the bromo source, an efficient­ and practical protocol for the synthesis of C3-brominated imidazo­[1,2-a]pyridines through ultrasound-promoted and Na2CO3-mediated regioselective bromination of imidazo[1,2-a]pyridines has been developed. This method effectively avoids the use of metal catalysts and harsh reaction conditions, and shows attractive characteristics

  摘要 通过使用三溴化吡啶鎓作为溴源，通过超声促进和Na 2 CO 3介导的咪唑并[1,2-]区域选择性溴化合成C3-溴化的咪唑并[1,2- a ]吡啶的有效而实用的方案。已经开发了α ]吡啶。该方法有效地避免了使用金属催化剂和苛刻的反应条件，并显示出引人注目的特性，例如操作简便，宽范围的基材范围以及良好至优异的收率，易于规模化生产和高能源效率。
• Copper-Mediated Aerobic Oxidative Synthesis of 3-Bromo-imidazo[1,2-<i>a</i>]pyridines with Pyridines and Enamides
  作者：Xiaoqiang Zhou、Hao Yan、Chaowei Ma、Yongqin He、Yamin Li、Jinhui Cao、Rulong Yan、Guosheng Huang

  DOI：10.1021/acs.joc.5b02384

  日期：2016.1.4

  A conversion of pyridines and enamides for the synthesis of 3-bromo-imidazo[1,2-c]pyridines was developed by copper-mediated aerobic oxidative coupling in a one-pot manner. This procedure tolerates various functional groups and affords a series of 3-bromo-imidazo[1,2-c]pyridines under mild conditions.