ethyl 6-methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylate | 1338469-68-3

• 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 6-methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylate
• 英文别名: Ethyl 6-methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylate
• CAS: 1338469-68-3
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: PVIYVQCGHBUUBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-2-propylimidazo[1,2-a]pyridine-3-carboxylate 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-(4-chlorophenoxy)ethyl)-6-methyl-2-propylimidazo[1,2-a]pyridine-3-carboxamide
  参考文献：
  名称：

  N-（2-苯氧基）乙基咪唑并[1,2 - a ]吡啶-3-羧酰胺类新型抗结核药的设计，合成及生物学活性

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2019.06.038
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.33h， 生成 ethyl 6-methyl-2-propylimidazo[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

• CBr₄ Mediated Oxidative C–N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines
  作者：Congde Huo、Jing Tang、Haisheng Xie、Yajun Wang、Jie Dong

  DOI：10.1021/acs.orglett.6b00137

  日期：2016.3.4

  tetrabromide mediated oxidative carbon–nitrogen bond formation of 2-aminopyridines or 2-aminopyrimidines with β-keto esters or 1,3-diones, leading to a variety of complex imidazo[1,2-α]pyridines or imidazo[1,2-α]pyrimidines, is reported. The reactions were realized under mild and metal-free conditions.

  四溴化碳介导的2-氨基吡啶或2-氨基嘧啶与β-酮酸酯或1,3-二酮的氧化碳-氮键形成，导致形成各种复杂的咪唑并[1,2-α]吡啶或咪唑并[1，报道了2-α]嘧啶。反应在温和且无金属的条件下进行。
• Synthesis of Imidazo[1,2-a]pyridines by the Bis(acetyloxy)(phenyl)-λ³-iodane-Mediated Oxidative Coupling of 2-Aminopyridines with β-Keto Esters and 1,3-Diones
  作者：Wei Yu、Xianpei Wang、Lijuan Ma

  DOI：10.1055/s-0030-1260106

  日期：2011.8

  2-aminopyridines and β-keto esters by using bis(acetyloxy)(phenyl)-λ³-iodane as an oxidant and boron trifluoride etherate as a catalyst. The amount of catalyst plays a key role in determining the course of the reaction. Whereas the use of 0.2 equivalents of catalyst ensures the generation of imidazo[1,2-a]pyridines, raising the amount of catalyst to 1.0 equivalents results in exclusive α-acetoxylation of

  咪唑并[1,2一]吡啶-3-羧酸盐，可直接由2-氨基吡啶和β酮酯通过使用双（乙酰基氧基）制备（苯基）-λ ³ -iodane作为氧化剂和三氟化硼醚作为催化剂。催化剂的量在确定反应过程中起关键作用。尽管使用0.2当量的催化剂可确保生成咪唑并[1,2- a ]吡啶，但将催化剂的量提高至1.0当量可导致β-酮酯的独家α-乙酰氧基化。2-氨基吡啶也可以与1，3-二酮反应，得到3-酰基咪唑并[1,2- a ]吡啶。 杂环-多环-环化-氧化-偶联
• TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones—synthesis of imidazo[1,2-a]pyridines
  作者：Lijuan Ma、Xianpei Wang、Wei Yu、Bing Han

  DOI：10.1039/c1cc13568f

  日期：——

  TBAI could catalyze the direct oxidative C–N coupling of 2-aminopyridines with β-keto esters and 1,3-diones, which affords imidazo[1,2-a]pyridines as the products. The reaction was realized under metal-free conditions by using tert-butyl hydroperoxide (TBHP) as the oxidant.

  TBAI可以催化2-氨基吡啶与β-酮酯和1,3-二酮的直接氧化C–N偶联反应，生成咪唑[1,2-a]吡啶作为产物。该反应在无金属条件下实现，采用叔丁基过氧化氢（TBHP）作为氧化剂。
• 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。
• 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.