2-methyl-3-(o-tolyl)imidazo[1,2-a]pyridine | 1366591-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-3-(o-tolyl)imidazo[1,2-a]pyridine
• CAS: 1366591-20-9
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: IRLMJBFZRYMMAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 2-methyl-3-(o-tolyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  咪唑并[1,2- a ]吡啶在C-3上通过铜（I）催化的C–H键官能化与芳基碘化物，溴化物和三氟甲磺酸酯直接芳构化

  摘要：

  开发了一种方便的方法，用于铜（I）催化的取代的咪唑并[1,2- a ]吡啶的芳基化。该方法适用于各种芳基亲电试剂，包括溴化物，碘化物和三氟甲磺酸酯。它代表了通过Cu（I）催化C-3取代的咪唑并[1,2- a ]吡啶的C-3芳构化的第一个通用方法，该反应构建了各种功能化的咪唑并[1,2- a ]吡啶的核π系统。

  DOI：

  10.1021/ol300232a

文献信息

• Transition-metal-free regioselective C–H halogenation of imidazo[1,2-<i>a</i>]pyridines: sodium chlorite/bromite as the halogen source
  作者：Junxuan Li、Jiayi Tang、Yuanheng Wu、Qiuxing He、Yue Yu

  DOI：10.1039/c7ra12100h

  日期：——

  facile transition-metal-free regioselective halogenation of imidazo[1,2-a]pyridines using sodium chlorite/bromite as the halogen source is presented. The reaction has provided an efficient method for the formation of C–Cl or C–Br bonds to synthesize 3-chloro or 3-bromo-imidazo[1,2-a]pyridines which were then efficiently transformed into imidazo[1,2-a]pyridine core π-systems by Suzuki–Miyaura reactions

  提出了一种使用亚氯酸钠/亚溴酸钠作为卤素源的咪唑并[1,2- a ]吡啶的简便的无过渡金属区域选择性卤化反应。该反应为形成C-Cl或C-Br键以合成3-氯或3-溴-咪唑并[1,2- a ]吡啶提供了一种有效的方法，然后将其有效转化为咪唑并[1,2- a ]吡啶核心π-系统通过铃木-宫浦反应。
• Highly regioselective palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids
  作者：Limin Zhao、Haiying Zhan、Jinqiang Liao、Jianping Huang、Qinlin Chen、Huifang Qiu、Hua Cao

  DOI：10.1016/j.catcom.2014.06.028

  日期：2014.11

  A highly regioselective method for the palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids has been developed by using O-2 as oxidant. This process can be applied to a wide range of imidazo[1,2-a]pyridines and arylboronic acids with excellent C-3-regioselectivity. It provides a new way for developing C-C bond-forming processes of multisubstituted imidazo[1,2-a]pyridines, which are common structural motifs in natural products and pharmaceuticals. (C) 2014 Elsevier B.V. All rights reserved.
• Highly regioselective C H bond functionalization of imidazo[1,2-a]pyridines with aryl halides catalyzed by Ru-arene complex
  作者：Hai Yang、Liping Yang、Yuan Li、Fan Zhang、Huajie Liu、Bing Yi

  DOI：10.1016/j.catcom.2012.04.032

  日期：2012.9

  An effective Ru-catalyzed coupling reaction of imidazo[1,2-a]pyridines and aryl halides is reported for the synthesis of polysubstituted imidazo[1,2-a]pyridines through C-H bond cleavages. The current study presents a convenient strategy to synthesize polysubstituted imidazo[1,2-a]pyridine, a common structural motif in natural products and pharmaceuticals. Desired products in considerable yields can be obtained in the presences of [RuCl2(P-cymene)](2) and Cs2CO3 in DMF at 120 degrees C after 15 h. (C) 2012 Elsevier B.V. All rights reserved.