7-methylbenzo[4,5]imidazo[1,2-a]pyridine | 1243272-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-methylbenzo[4,5]imidazo[1,2-a]pyridine
• 英文别名: 7-Methylbenzo[4,5]imidazo[1,2-a]pyridine；7-methylpyrido[1,2-a]benzimidazole
• CAS: 1243272-98-1
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: QHABOBYYPJQRDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯-5-甲基苯胺 在 potassium tert-butylate 、 氨 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 7-methylbenzo[4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions

  摘要：

  The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido [1,2-a]benzimidazoles via S(RN)1 mediated C-N bond forming reactions in moderate to excellent yields (58-94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C-C bond formation generating 7H-indolo[2,3-c]isoquinoline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.087

文献信息

• A Metal-Free Tandem Demethylenation/C(sp²)–H Cycloamination Process of <i>N</i>-Benzyl-2-aminopyridines via C–C and C–N Bond Cleavage
  作者：Dongdong Liang、Yimiao He、Lanying Liu、Qiang Zhu

  DOI：10.1021/ol4015656

  日期：2013.7.5

  A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C–C and C–N bond cleavage.

  已经开发了一种轻度，无金属的合成方法，该方法以N-苄基-2-氨基吡啶为原料，以PhI（OPiv）2为化学计量氧化剂，合成了吡啶并[1,2- a ]苯并咪唑类化合物。该过程由一个不寻常的岛（OPiv）发起2介导的本位小号ë的Ar反应，接着进行溶剂辅助C-C和C-N键断裂。
• A Direct Intramolecular C−H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2-<i>a</i>]benzimidazoles from <i>N</i>-Aryl-2-aminopyridines
  作者：Honggen Wang、Yong Wang、Changlan Peng、Jiancun Zhang、Qiang Zhu

  DOI：10.1021/ja1067993

  日期：2010.9.29

  A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)(2) and Fe(NO(3))(3)·9H(2)O, is carried out in DMF under a dioxygen atmosphere. Diversified pyrido[1,2-a]benzimidazoles containing various substitution patterns are obtained in moderate to excellent yields

  已经开发了一种通过 N-芳基-2-氨基吡啶的直接分子内芳香族 CH 胺化来合成吡啶并 [1,2-a] 苯并咪唑的新型高效合成方法。该反应由 Cu(OAc)(2) 和 Fe(NO(3))(3)·9H(2)O 共同催化，在双氧气氛下在 DMF 中进行。使用该方法可以以中等至极好的收率获得含有各种取代模式的多样化吡啶并[1,2-a]苯并咪唑。机理研究结果表明，Cu(III) 催化的亲电芳香取代 (S(E)Ar) 途径在此过程中起作用。铁 (III) 的独特作用被认为在于它能够促进更具亲电性的铜 (III) 物质的形成。在没有铁 (III) 的情况下，会发生效率低得多且可逆的 Cu(II) 介导的 S(E)Ar 过程。
• Copper Acetate Aerobic Oxidative Synthesis of Pyrido[1,2-a]benzimidazoles from Aminopyridines and Phenylboronic Acids
  作者：Hao Yan、Hui Guo、Xiaoqiang Zhou、Zhenyu Zuo、Jingli Liu、Guanghui Zhang、Shuan Zhang

  DOI：10.1055/s-0037-1611847

  日期：2019.7

  2-a]benzimidazoles, which show interesting and potentially useful biological activities, have drawn extensive attention from chemists. A straightforward copper acetate-oxidative one-pot synthesis of these compounds from 2-aminopyridines and phenylboronic acids through C–N bond formation and C–H bond activation was developed as a simple and convenient method.

  吡啶并[1,2-a]苯并咪唑显示出有趣且潜在有用的生物活性，引起了化学家的广泛关注。通过 C-N 键形成和 C-H 键活化，从 2-氨基吡啶和苯基硼酸中直接通过乙酸铜氧化一锅法合成这些化合物是一种简单方便的方法。
• Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions
  作者：Yanjun Xie、Jun Wu、Xingzong Che、Ya Chen、Huawen Huang、Guo-Jun Deng

  DOI：10.1039/c5gc01978h

  日期：——

  Pyrido[1,2-a]benzimidazole derivatives were selectively prepared from 2-aminopyridines and cyclohexanones under metal free conditions.

  通过无金属条件下，从2-氨基吡啶和环己酮选择性地制备了吡啶并咪唑衍生物。
• Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission
  作者：Dongbing Zhao、Junyi Hu、Ningjie Wu、Xiaolei Huang、Xurong Qin、Jingbo Lan、Jingsong You

  DOI：10.1021/ol202807d

  日期：2011.12.16

  A palladium-catalyzed two or fourfold amination was established that allows regiospecific synthesis of a diversity-oriented library of 1,2-disubstituted (hetero)aryl fused imidazoles, and provides an exceptional tool for the discovery of fluorescent scaffolds with tunable fluorescence emission. These fluorophores have been applied as fluorescent probes for live cell imaging.

  建立了钯催化的两倍或四倍胺化反应，该反应可以区域特异性合成1,2-二取代（杂）芳基稠合的咪唑的多样性导向文库，并为发现具有可调荧光发射的荧光支架提供了出色的工具。这些荧光团已被用作活细胞成像的荧光探针。