2-(3-trifluoromethyl-phenyl)-imidazo[1,2-a] pyridine

• 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-(3-trifluoromethyl-phenyl)-imidazo[1,2-a] pyridine
• 英文别名: 2-[3-(Trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
• 化学式: C₁₄H₉F₃N₂
• 分子量: 262.234
• InChiKey: MGWGPKPUUGBGQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-trifluoromethyl-phenyl)-imidazo[1,2-a] pyridine 在 亚硝酸 作用下， 以90%的产率得到3-nitroso-2-(3'-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Anti-anxiety and sedative profile evaluation of imidazo[1,2-a]pyridine derivatives

  摘要：

  AbstractThree imidazo[1,2‐a]pyridine‐3‐nitrosated (L‐1, L‐2, L‐3) and a 3‐formyl imidazo[1,2‐a]pyridine thiosemicarbazone (L‐4) were synthesized and evaluated for their effects in the elevated plus maze, burying behavior test, rotarod performance, the horizontal wire test, and locomotor activity. L‐2 and L‐3 increased the percent time spent in the open arms of the plus maze at doses of 1 and 2 mg/kg without modifying the number of total entries. In addition, L‐2 and L‐3 (1 mg/kg) increased the number of open arm entries indicating anxiolytic‐like activity at this dose. In the burying behavioral test, L‐1 (2–8 mg/kg), L‐2 (8 mg/kg), and L‐3 (4 and 8 mg/kg), induced a clear reduction in cumulative burying behavior, without modifying burying behavior latency, thus reducing experimental anxiety. In the rotarod test, L‐1 and L‐2 impaired rotarod performance only at the highest evaluated dose (64 mg/kg) at which reduction of motor activity was observed and thereby no conclusions about myorelaxant effects can be proposed. All compounds showed a clear sedative effect and corresponding ED50 values were obtained. Results indicate that compounds L‐1, L‐2, and L‐3 show a sedative and an anxiolytic profile. Drug Dev Res 71:371–381, 2010. © 2010 Wiley‐Liss, Inc.

  DOI：

  10.1002/ddr.20382
• 作为产物：
  描述：

  2-氨基吡啶 、 间三氟甲基苯乙酮 在 iron(III) chloride hexahydrate 、 碘 、 氧气 作用下， 以 氯苯 为溶剂， 反应 20.0h， 以50%的产率得到2-(3-trifluoromethyl-phenyl)-imidazo[1,2-a] pyridine
  参考文献：
  名称：

  铁/碘催化的Ortoleva-King型规程新颖的一步合成咪唑并[1,2- a ]吡啶和唑来oli的方法

  摘要：

  咪唑并[1,2- a ]吡啶因其多种生物活性而在制药工业中形成多功能支架。因此，这些分子的合成引起了极大的兴趣，并导致了许​​多新方法的发展。在这里，我们描述了第一个铁催化的Ortoleva-King型协议，以合成这些稠合的杂环化合物。该方法采用廉价且容易获得的FeCl 3 ·6H 2 O和分子碘作为催化体系。该过程已被基板范围与各种芳族酮和2-氨基吡啶，得到不同的咪唑并延伸[1,2被很好探索一个吡啶衍生物的产率中等至良好。该方案的成功应用还通过直接一步合成胃保护药物Zolimidine得到了证明。

  DOI：

  10.1016/j.tetlet.2019.150950

文献信息

• H₂O₂/DMSO-Promoted Regioselective Synthesis of 3,3′-Bisimidazopyridinylmethanes via Intermolecular Oxidative C(sp²)–H Bond Activation of Imidazoheterocycles
  作者：Om P. S. Patel、Devireddy Anand、Rahul K. Maurya、Prem P. Yadav

  DOI：10.1021/acs.joc.6b01355

  日期：2016.9.2

  under air. A library of 3,3′-bis(2-arylimidazo[1,2-a]pyridin-3-yl)methanes has been achieved in good to excellent yields. The present methodology has been successfully applied to imidazo[2,1-b]thiazoles and imidazo[2,1-b]benzothiazoles. Furthermore, the current approach was also extended for the synthesis of unsymmetrical 3,3′-bisimidazopyridinylmethanes under optimized reaction conditions. A mechanistic

  在过去的十年中，无金属的C–C键形成方法因其易用性和低成本而备受关注。该报告代表了一种新的，无金属的3,3'-双咪唑并吡啶甲基甲烷的合成方法，该方法是通过咪唑并[1,2- a ]吡啶的分子间氧化C（sp 2）-H键分子间氧化，并以二甲基亚砜作为碳合成子（CH 2）在空气中使用H 2 O 2作为温和的氧化剂。已经获得了3,3'-双（2-芳基咪唑并[1,2- a ]吡啶-3-基）甲烷的文库，收率良好至极佳。本方法已成功地应用于咪唑并[2,1- b ]噻唑和咪唑并[2,1- b]苯并噻唑。此外，当前的方法也扩展到在优化的反应条件下合成不对称的3,3'-双咪唑并吡啶基甲烷。根据自由基清除剂的实验，DMSO- d 6和ESI-MS的观察结果，提出了一种机理途径。
• Heterogeneously copper-catalyzed oxidative synthesis of imidazo[1,2-a]pyridines using 2-aminopyridines and ketones under ligand- and additive-free conditions
  作者：Xu Meng、Yanmin Wang、Chaoying Yu、Peiqing Zhao

  DOI：10.1039/c4ra03299c

  日期：——

  and mild heterogeneously CuCl2/nano-TiO2-catalyzed aerobic synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and ketones has been developed using air as the oxidant in the absence of any ligands and additives. This strategy was compatible with a large range of substrates, including unactivated aryl ketones and unsaturated ketones and went through the C–H bond functionalization mechanism instead

  利用空气作为氧化剂，在不存在任何配体和添加剂的情况下，开发了一种高效，温和的，异质性的CuCl 2 /纳米TiO 2催化的由2-氨基吡啶和酮类咪唑并[1,2- a ]吡啶的好氧合成方法。这个策略是具有大范围的底物相容的，包括未活化的芳基酮和不饱和酮，并通过C-H键的官能机构去的，而不是我- -assisted Ortoleva景反应以提供相应的咪唑并[1,2一以较低的催化剂负载量（0.8摩尔％）获得高产率的对吡啶。而且，该非均相催化剂可以成功地用于克规模的合成中并且可以多次重复使用而不会显着降低催化活性。
• Nickel-Catalyzed C-H Trifluoromethylation of Electron-Rich Heteroarenes
  作者：Yun Wu、Hao-Ran Zhang、Ruo-Xing Jin、Quan Lan、Xi-Sheng Wang

  DOI：10.1002/adsc.201600702

  日期：2016.11.17

  The first example of a nickel‐catalyzed C–H trifluoromethylation of electron‐rich heteroarenes, including imidazopyridines, indoles and thiophenes, has been developed with the commercially available and relatively inexpensive industrial raw material iodotrifluoromethane (CF3I) as the trifluoromethylating reagent. The synthetic potential of this method is demonstrated by its successful application to

  富电子杂芳烃（包括咪唑并吡啶，吲哚和噻吩）的镍催化CH-H三氟甲基化的第一个例子是用市售且相对便宜的工业原料碘代三氟甲烷（CF 3 I）作为三氟甲基化试剂而开发的。该方法的合成潜力已成功应用于生物活性分子褪黑激素和佐米曲普坦的直接三氟甲基化。
• Catalyst-free, visible-light-induced direct radical cross-coupling perfluoroalkylation of the imidazo[1,2-<i>a</i>]pyridines with perfluoroalkyl iodides
  作者：Jinbo Huang、Dandan Wu、Xiaokang Bai、Panyuan Cai、Wei-Guo Zhu

  DOI：10.1039/d1nj00651g

  日期：——

  A mild and eco-friendly visible-light-induced direct radical cross-coupling perfluoroalkylation of the imidazo[1,2-a]pyridines with perfluoroalkyl iodides was established. This method leads to a facile and practical synthesis of valuable 3-perfluoroalkyl substituted imidazo[1,2-a]pyridines in moderate to excellent yields and features a broad substrate scope and wide functional group tolerance. Moreover

  建立了一种温和且环保的可见光诱导的咪唑并[1,2- a ]吡啶与全氟烷基碘的全氟烷基直接自由基交叉偶联。该方法导致以中等至优异的产率容易且实用地合成有价值的3-全氟烷基取代的咪唑并[1,2- a ]吡啶，并且具有宽的底物范围和宽的官能团耐受性。此外，已经进行了对照实验，表明了反应机理中涉及的自由基途径。
• Substituted imidazo[1,2-A] pyridine derivatives
  申请人：——

  公开号：US20020188128A1

  公开（公告）日：2002-12-12

  The present invention is a series of novel compounds of formula I and a method of treatment or prevention of a mGluR5 receptor mediated disease by administering an therapeutically effective amount of a compound formula 1 wherein R 1 and R 2 are selected from hydrogen, (C 1-6 )-alkyl, halogen, hydroxy, (C 1-6 )-alkoxy and A is defined the description, or a pharmaceutically acceptable salt thereof.

  本发明涉及一系列新颖的化合物，化学式为I，并通过给予有效治疗剂量的化合物化学式1来治疗或预防mGluR5受体介导的疾病的方法，其中R1和R2从氢、(C1-6)-烷基、卤素、羟基、(C1-6)-烷氧基中选择，A在描述中有定义，或其药用盐。