3-(1,2-dimethyl-1H-imidazol-5-yl)quinoline | 1201005-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(1,2-dimethyl-1H-imidazol-5-yl)quinoline
• 英文别名: 3-(2,3-Dimethylimidazol-4-yl)quinoline；3-(2,3-dimethylimidazol-4-yl)quinoline
• CAS: 1201005-82-4
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: ZKHPXMOEHJXFJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基咪唑 、 3-溴喹啉 在 C₂₄H₂₂ClN₃OPdSe 、 potassium carbonate 、 三甲基乙酸 作用下， 以 二甲胺 为溶剂， 反应 10.0h， 以92%的产率得到3-(1,2-dimethyl-1H-imidazol-5-yl)quinoline
  参考文献：
  名称：

  硫磺化的乙酰胺官能化的1 H-苯并咪唑鎓盐衍生的N-杂环碳酰胺的钯（II）配合物：有氧条件下咪唑区域选择性酰化的可回收催化剂

  摘要：

  所述chalcogenated乙酰胺官能化的1个ħ -benzimidazolium盐前体[1-（CH 2 C（O）NH（CH 2）2 S / SEPH）-3- RC 7 ħ 5 Ñ 2 ] + X ̅（L1 - L4 ; R ＝ Me，CH 2 Ph； X ＝ Br，I）至C，N̅，S / Se配体通过1 H-苯并咪唑与2-溴-N -（-（2-苯硫基/硒代）乙基）乙酰胺（A1 / A2），然后用甲基/苄基溴/碘化物处理。L1 – L4的反应用Ag 2 O进行处理，然后用[Pd（CH 3 CN）2 Cl 2 ]处理，生成复合物[Pd（C，N̅，E）Cl]（C1 - C4），其中C，N –，E钳制配体源自L1-L4。L1 - L4和C1 - C4通过元素分析，HR-MS和1 H，13 C { 1 H}和77 Se { 1 H} NMR光谱进行了表征。L2和C1 - C3的单晶结构通过X射线衍

  DOI：

  10.1021/acs.organomet.8b00246

文献信息

• Palladium(II) Complexes of N-Heterocyclic Carbene Amidates Derived from Chalcogenated Acetamide-Functionalized 1<i>H</i>-Benzimidazolium Salts: Recyclable Catalyst for Regioselective Arylation of Imidazoles under Aerobic Conditions
  作者：Renu Bhaskar、Alpesh K. Sharma、Ajai K. Singh

  DOI：10.1021/acs.organomet.8b00246

  日期：2018.8.27

  [1-(CH2C(O)NH(CH2)2S/SePh)-3-R-C7H5N2]+ X̅ (L1–L4; R = Me, CH2Ph; X = Br, I) to C,N̅,S/Se ligands were synthesized by reaction of 1H-benzimidazole with 2-bromo-N-(2-phenylthio/seleno)ethyl)acetamide (A1/A2), followed by treatment with methyl/benzyl bromide/iodide. The reaction of L1–L4 with Ag2O followed by treatment with [Pd(CH3CN)2Cl2] resulted in complexes [Pd(C,N̅,E)Cl] (C1–C4), where the C,N–,E pincer

  所述chalcogenated乙酰胺官能化的1个ħ -benzimidazolium盐前体[1-（CH 2 C（O）NH（CH 2）2 S / SEPH）-3- RC 7 ħ 5 Ñ 2 ] + X ̅（L1 - L4 ; R ＝ Me，CH 2 Ph； X ＝ Br，I）至C，N̅，S / Se配体通过1 H-苯并咪唑与2-溴-N -（-（2-苯硫基/硒代）乙基）乙酰胺（A1 / A2），然后用甲基/苄基溴/碘化物处理。L1 – L4的反应用Ag 2 O进行处理，然后用[Pd（CH 3 CN）2 Cl 2 ]处理，生成复合物[Pd（C，N̅，E）Cl]（C1 - C4），其中C，N –，E钳制配体源自L1-L4。L1 - L4和C1 - C4通过元素分析，HR-MS和1 H，13 C 1 H}和77 Se 1 H} NMR光谱进行了表征。L2和C1 - C3的单晶结构通过X射线衍
• Phosphine-free palladium-catalysed direct 5-arylation of imidazole derivatives at low catalyst loading
  作者：Julien Roger、Henri Doucet

  DOI：10.1016/j.tet.2009.09.084

  日期：2009.11

  The regioselective 5-arylation of imidazole derivatives with aryl bromides using a low loading of a phosphine-free palladium catalyst gives a simple and economic access to the corresponding 5-arylimidazoles. The choice of the base and of the solvent was found to be crucial to form these products in high yields. Using KOAc as the base, DMAc as the solvent and only 0.5–0.01 mol % Pd(OAc)2 as the catalyst

  使用低负荷的无膦钯催化剂，将咪唑衍生物与芳基溴进行区域选择性的5-芳基化，可简单而经济地获得相应的5-芳基咪唑。发现碱和溶剂的选择对于以高收率形成这些产物是至关重要的。使用KOAc作为碱，使用DMAc作为溶剂，仅使用0.5-0.01 mol％Pd（OAc）2作为催化剂，可以以中等到良好的收率得到目标产物，并带有多种芳基溴化物。芳基溴上的取代基如氟，三氟甲基，甲酰基，乙酰基，丙酰基，酯或腈是可以接受的。也可以使用立体上稠合的芳基溴化物或杂芳基溴化物。咪唑衍生物上取代基的性质对产率有重要影响。
• Palladium-catalysed direct arylations of heteroaromatics using more eco-compatible solvents pentan-1-ol or 3-methylbutan-1-ol
  作者：Souhila Bensaid、Nouria Laidaoui、Douniazad El Abed、Soufi Kacimi、Henri Doucet

  DOI：10.1016/j.tetlet.2011.01.084

  日期：2011.3

  The palladium-catalysed direct coupling of aryl halides with heteroaromatics in greener solvents than DMF or DMAc, which are often employed for such couplings, would be a considerable advantage for both industrial application and sustainable development. We observed that a range of aryl bromides undergoe coupling via C-H bond activation/functionalisation reaction of thiazoles or imidazoles in moderate to good yields using pentan-1-ol or 3-methylbutan-1-ol as the solvents. Pentan-1-ol and 3-methylbutan-1-ol are less toxic than DMF or DMAc, moreover they are bioresources as they can be obtained by fermentation. Therefore, these reaction conditions are certainly more eco-compatible than those generally employed for such couplings. (C) 2011 Elsevier Ltd. All rights reserved.
• Developing Bis(imino)acenaphthene-Supported <i>N</i>-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles
  作者：Li-Qun Hu、Rong-Li Deng、Yan-Fen Li、Cui-Jin Zeng、Dong-Sheng Shen、Feng-Shou Liu

  DOI：10.1021/acs.organomet.7b00784

  日期：2018.1.22

  On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation of azoles. The effect of backbone and N-moieties on NHCs was evaluated, and the reaction conditions were optimized. It was found that the bulky Pd-PEPPSI complexes could be successfully employed in cross-coupling of (hetero)aryl bromides with azoles at a low palladium loading of 0.5-0.05 mol % under aerobic conditions, demonstrating the ease of manipulation without glovebox and handling of solvents.