ethyl 2,8-dimethylimidazo[1,2-a]pyridine-3-carboxylate | 241146-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: ethyl 2,8-dimethylimidazo[1,2-a]pyridine-3-carboxylate
• CAS: 241146-66-7
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: LALYREKEVNEKCM-UHFFFAOYSA-N

物化性质

• 熔点：
  79-82°

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  ethyl 2,8-dimethylimidazo[1,2-a]pyridine-3-carboxylate 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,8-二甲基咪唑并[1,2-a]吡啶-3-羧酸
  参考文献：
  名称：

  使用 Rh(III) 催化对咪唑并[1,2-a]吡啶-3-甲酰胺进行定向区域选择性芳基化

  摘要：

  与之前报道的在 C-5 中心功能化咪唑并[1,2- a ]吡啶的自由基途径相比，指导基团方法很少见。在此，我们展示了一种铑（ III ）催化的高效和区域选择性策略，用于使用N-甲氧基酰胺作为定向基团对咪唑并[1,2- a ]吡啶进行定向C-5官能化。该方法有利于定向芳基化，无需预功能化。它还允许进行克级合成和后功能化。

  DOI：

  10.1039/d4ob01166j
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 反应 0.5h， 以41%的产率得到ethyl 2,8-dimethylimidazo[1,2-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Microwave Assisted Synthesis of Disubstituted Imidazo[1,2-a]pyridine-3-carboxylic Acid Esters

  摘要：

  A novel and efficient synthetic method leveraging microwave-assisted organic synthesis (MAOS) to prepare disubstituted imidazo[1,2-a]pyridine-3-carboxylic acid esters (IPCEs) (3a-z), the key intermediates for a class of novel anti-tuberculosis agents, is reported. Under microwave heating at 120 degrees C for 20 or 30 min, the condensations of 2-aminopyridines (1a-k) and ethyl 2-halogenated acetoacetates (2a-d) were conveniently performed in ethanol with acceptable yields.

  DOI：

  10.3987/com-15-13299

文献信息

• Photocatalytic regeneration of brominating agent in the visible light-mediated synthesis of imidazo[1,2-<i>a</i>]pyridines
  作者：Irwan Iskandar Roslan、Kian-Hong Ng、Stephan Jaenicke、Gaik-Khuan Chuah

  DOI：10.1039/c9cy00141g

  日期：——

  supporting evidence of a reductive quenching pathway. The avoidance of stoichiometric excess of the halogen or peroxide oxidants for halide regeneration makes this protocol an environmentally-friendly synthesis with low E-factor.

  在可见光介导的光催化下，将1，3-二羰基与2-氨基吡啶偶联可以得到各种各样的咪唑并[1,2- a ]吡啶。使用便宜的和可商购的荧光素染料赤藓红B作为光氧化还原催化剂，KBr作为卤化剂进行原位溴化。该方案的特征在于使用催化量的卤化剂，该卤化剂由光催化剂在可见光照射下再生。循环伏安法研究提供了还原性淬灭途径的支持证据。避免化学计量过量的卤素或过氧化物氧化剂用于卤化物的再生，使该方案成为具有低E因子的环境友好的合成方法。
• Design, synthesis and biological activity of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides as new antitubercular agents
  作者：Apeng Wang、Kai Lv、Linhu Li、Hongtao Liu、Zeyu Tao、Bin Wang、Mingliang Liu、Chao Ma、Xican Ma、Bing Han、Aoyu Wang、Yu Lu

  DOI：10.1016/j.ejmech.2019.06.038

  日期：2019.9

  A series of N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides (IPAs), based on the structure of WZY02 discovered in our lab, were designed and synthesized as new anti-TB agents. Results reveal that many of them exhibit excellent in vitro inhibitory activity with low nanomolar MIC values against both drug-sensitive MTB strain H37Rv and drug-resistant clinical isolates. Compounds 15b and 15d display

  根据在我们实验室中发现的WZY02的结构，设计并合成了一系列N-（2-苯氧基）乙基咪唑并[1,2 - a ]吡啶-3-甲酰胺（IPAs），作为新型抗结核药物。结果表明，它们中的许多对药物敏感性MTB菌株H37Rv和耐药性临床分离株均表现出优异的体外抑制活性，且纳摩尔摩尔MIC值低。化合物15b和15d显示出良好的安全性和药代动力学特征，表明它们有望成为未来抗结核药物发现的先导化合物。
• Advancement of Imidazo[1,2-<i>a</i>]pyridines with Improved Pharmacokinetics and nM Activity vs. <i>Mycobacterium tuberculosis</i>
  作者：Garrett C. Moraski、Lowell D. Markley、Jeffrey Cramer、Philip A. Hipskind、Helena Boshoff、Mai A. Bailey、Torey Alling、Juliane Ollinger、Tanya Parish、Marvin J. Miller

  DOI：10.1021/ml400088y

  日期：2013.7.11

  A set of 14 imidazo[1,2-a]pyridine-3-carboxamides was synthesized and screened against Mycobacterium tuberculosis H(37)Rv. The minimum inhibitory concentrations of 12 of these agents were <= 1 mu M against replicating bacteria and 5 compounds (9, 12, 16, 17, and 18) had MIC values <= 0.006 mu M. Compounds 13 and 18 were screened against a panel of MDR and XDR drug resistant clinical Mtb strains with the potency of 18 surpassing that of clinical candidate PA-824 by nearly 10-fold. The in vivo pharmacokinetics of compounds 13 and 18 were evaluated in male mice by oral (PO) and intravenous (IV) routes. These results indicate that readily synthesized imidazo[1,2-a]pyridine-3-carboxamides are an exciting new class of potent, selective anti-TB agents that merit additional development opportunities.
• Microwave Assisted Synthesis of Disubstituted Imidazo[1,2-a]pyridine-3-carboxylic Acid Esters
  作者：Ming-liang Liu、Qiu-rong Zhang、Lin-hu Li、Zhao-yang Wu、Zhuo-rong Li、Hui-yuan Guo

  DOI：10.3987/com-15-13299

  日期：——

  A novel and efficient synthetic method leveraging microwave-assisted organic synthesis (MAOS) to prepare disubstituted imidazo[1,2-a]pyridine-3-carboxylic acid esters (IPCEs) (3a-z), the key intermediates for a class of novel anti-tuberculosis agents, is reported. Under microwave heating at 120 degrees C for 20 or 30 min, the condensations of 2-aminopyridines (1a-k) and ethyl 2-halogenated acetoacetates (2a-d) were conveniently performed in ethanol with acceptable yields.
• 10.1039/d4ob01166j
  作者：Jahan, Kousar、Sood, Mehak、Jain, Osheen、Sahoo, Subash C.、Bharatam, Prasad V.

  DOI：10.1039/d4ob01166j

  日期：——

  In contrast to previously reported free-radical pathways to functionalize imidazo[1,2-a]pyridines at the C-5 centre, directing group approaches are rare. Herein, we demonstrate a rhodium(III) catalyzed efficient and regioselective strategy for directed C-5 functionalization of imidazo[1,2-a]pyridines using N-methoxyamide as a directing group. This methodology facilitates directed arylation without

  与之前报道的在 C-5 中心功能化咪唑并[1,2- a ]吡啶的自由基途径相比，指导基团方法很少见。在此，我们展示了一种铑（ III ）催化的高效和区域选择性策略，用于使用N-甲氧基酰胺作为定向基团对咪唑并[1,2- a ]吡啶进行定向C-5官能化。该方法有利于定向芳基化，无需预功能化。它还允许进行克级合成和后功能化。