3-(1H-benzimidazol-2-yl)-2-chloro-6-methyl-quinoline | 107607-76-1

• 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-(1H-benzimidazol-2-yl)-2-chloro-6-methyl-quinoline
• 英文别名: 3-(1H-benzimidazol-2-yl)-2-chloro-6-methylquinoline
• CAS: 107607-76-1
• 化学式: C₁₇H₁₂ClN₃
• 分子量: 293.755
• InChiKey: UCYJLOZUDSCNCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-benzimidazol-2-yl)-2-chloro-6-methyl-quinoline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 2-methylbenzo[4',5']imidazo[1',2':1,4]azeto[2,3-b]quinoline
  参考文献：
  名称：

  One-Pot Synthesis of Novel Quinoline-Fused Azeto[1,2-a]benzimidazole Analogs Via Intramolecular Pd-Catalyzed C–N Coupling

  摘要：

  A common strategy to incorporate four-membered ring system between benzimidazole and quinoline cores was developed by one-pot protocol involving the condensation of o-phenylenediamine with 2-chloroquinoline-3-carbaldehyde derivatives followed by intramolecular palladium catalyzed C-N coupling. A series of ligands, palladium sources, bases and solvents were screened to optimize the reaction conditions for the synthesis of quinoline-fused azeto[1,2-a]benzimidazoles.An efficient catalytic system for the introduction of 4-membered-ring system between benzimidazole and quinoline cores has been developed by one-pot intramolecular C-N coupling of o-phenylenediamine with 6-substituted-2-chloroquinoline-3-carbaldehydes.

  DOI：

  10.1007/s10562-014-1266-9
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 6.03h， 生成 3-(1H-benzimidazol-2-yl)-2-chloro-6-methyl-quinoline
  参考文献：
  名称：

  Design and synthesis of luotonin A-derived topoisomerase targeting scaffold with potent antitumor effect and low genotoxicity

  摘要：

  DOI：

  10.1016/j.bioorg.2023.107015

文献信息

• The Synthesis of Benzimidazole Derivatives in the Absence of Solvent and Catalyst
  作者：Chuanming Yu、Peng Guo、Can Jin、Weike Su

  DOI：10.3184/030823409x447763

  日期：2009.5

  Differently substituted benzimidazoles have been synthesised from o-phenylenediamine and arylaldehydes or arylmethylene-malononitriles absorbed on silica gel. The reaction was carried out by intermittent grinding or by a microwave-assisted technique under solvent- and catalyst-free conditions giving good yields of the products.

  在硅胶上吸收邻苯二胺和芳基醛或芳基亚甲基丙二腈合成了不同取代的苯并咪唑。反应是在无溶剂和催化剂的条件下，通过间歇研磨或微波辅助技术进行的，产物收率很高。
• Benzimidazole quinoline derivatives — An effective green fluorescent dye for bacterial imaging
  作者：Mahalingam Malathi、Palathurai Subramaniam Mohan、Raymond J. Butcher、Chidambaram Kulandaisamy Venil

  DOI：10.1139/v09-139

  日期：2009.12

  A one-pot synthesis of benzimidazoles by condensing naphthyl or quinoline aldehyde with benzene-1,2-diamine has been reported. IR, ¹H and ¹³C NMR, mass spectral, and CHN analyses were used to elucidate the structures of the products. The molecular structural correlation in the optical properties of the quinoline and naphthalene benzimidazoles was explored. The fluorescence quantum yield ([Formula: see text]) and time-resolved fluorescent lifetime of the quinoline benzimidazoles derivatives were estimated. The influence of solvent polarity and pH on the optical property of quinoline derivatives was illustrated. To explore the bioanalytical applicability, the thermal stability by TG–DTA analysis and the cytogenetic analysis of 3-(1H-benzoimidazol-2-yl)-2-chloro-8-methyl-quinoline (1b) compound were carried out. The fluorescent staining ability of 1b was analyzed and also compared with the normal Gram staining in the bacterium.

  本研究报道了一种通过萘醛或喹啉醛与苯-1,2-二胺缩合的苯并咪唑的单锅合成方法。通过红外光谱、1H 和 13C NMR、质谱和 CHN 分析，阐明了产物的结构。研究还探讨了喹啉和萘苯并咪唑光学性质中的分子结构相关性。估算了喹啉苯并咪唑衍生物的荧光量子产率（[式：见正文]）和时间分辨荧光寿命。研究还说明了溶剂极性和 pH 值对喹啉衍生物光学性质的影响。为了探索喹啉衍生物的生物分析应用性，研究人员对 3-(1H-苯并咪唑-2-基)-2-氯-8-甲基喹啉（1b）化合物进行了 TG-DTA 热稳定性分析和细胞遗传学分析。对 1b 的荧光染色能力进行了分析，并与细菌的正常革兰氏染色进行了比较。
• High catalytic performance of CoCuFe2O4/ZIF-8(Zn) nanocatalyst for synthesis of new benzimidazole derivatives
  作者：Firouz Matloubi Moghaddam、Atefeh Jarahiyan、Mahdi Heidarian Haris、Parisa Yaqubnezhad Pazoki、Bagher Aghamiri

  DOI：10.1016/j.molstruc.2023.135496

  日期：2023.8

  microscopy (TEM) were used to characterize the catalyst structure. This catalytic system gave us a satisfactory answer and provided the corresponding products with excellent yields. In order to implement procedures to comply with green chemistry, water was used for the synthesis of both catalyst and benzimidazole (benzimidazole-quinoline, benzothiazole, and benzoxazole) derivatives. This publication is

  在此，我们报道了一种高效的催化体系，用于在绿色条件下通过芳基醛和邻苯二胺（2-氨基苯硫酚、2-氨基苯酚）之间的反应快速构建苯并咪唑、苯并咪唑-喹啉、苯并噻唑和苯并恶唑衍生物。借助十六烷基三甲基溴化铵 (CTAB) 结合 CoCuFe 2 O 4 和 ZIF-8(Zn)，通过简单易行的程序合成了磁性 CoCuFe 2 O 4 / ZIF - 8 ( Zn ) 。不同的技术，如傅里叶透射红外光谱 (FT-IR)、X射线衍射 (XRD)、场发射扫描电子显微镜 (FESEM) 和透射电子显微镜 (TEM) 用于表征催化剂结构。该催化体系给了我们一个满意的答案，并提供了具有优异产率的相应产品。为了实施符合绿色化学的程序，水用于合成催化剂和苯并咪唑（苯并咪唑-喹啉、苯并噻唑和苯并恶唑）衍生物。该出版物是第一个在室温下无需苛刻条件下快速合成苯并咪唑（苯并咪唑-喹啉、苯并噻唑和苯并恶唑）衍生物的简单方案。
• DBUHI3 complex an efficient catalyst for the synthesis of 2-phenyl benzimidazole and benzothiazole derivatives
  作者：Ramesh Gawade、Pramod Kulkarni

  DOI：10.2298/jsc220526007g

  日期：——

  Herein, we have reported the facile synthesis of various benzimidazole/ benzothiazole by using DBU?iodine?iodide as a green and simple catalyst. The R3NHI3 complexes have been formed by reacting an aqueous mixture of ammonium iodide and molecular iodine with the aqueous solution of amine. The structure of R3NHI3 complexes has been confirmed by spectroscopic techniques. The prepared amine?iodine complexes were screened as a catalysts in the synthesis of benzimidazole/benzothiazoles. Among the screened catalysts DBUHI3 complex has been found as most efficient catalyst. The synthesis of benzimidazoles and benzothiazoles has been achieved with the reaction of ophenylene diamine/o-aminothiophenol and various substituted aryl aldehyde using DBUHI3 as a catalyst. The present protocol has offered some advantages over other reported protocols such as the mild reaction condition, commercially available precursors, inexpensive catalyst, short reaction time, the broad scope of the substrate, high yield, simple isolation of the product and environmentally benign method.

  在此，我们报告了利用 DBU?碘?碘化物作为绿色简易催化剂，轻松合成各种苯并咪唑/苯并噻唑的过程。碘化铵和分子碘的水混合物与胺的水溶液反应生成了 R3NHI3 复合物。R3NHI3 复合物的结构已通过光谱技术得到证实。所制备的胺碘配合物被筛选用作合成苯并咪唑/苯并噻唑的催化剂。在筛选出的催化剂中，发现 DBUHI3 复合物是最有效的催化剂。以 DBUHI3 为催化剂，通过亚苯基二胺/邻氨基苯硫酚和各种取代的芳基醛的反应，实现了苯并咪唑和苯并噻唑的合成。与其他已报道的方案相比，本方案具有一些优势，如反应条件温和、前体可从市场上买到、催化剂价格低廉、反应时间短、底物范围广、产率高、产物分离简单以及方法对环境无害。
• Bhanumathi, Nanduri; Rao, Kakulapati Rama; Sattur, Prahlad Balvantrao, Heterocycles, 1986, vol. 24, # 6, p. 1683 - 1685
  作者：Bhanumathi, Nanduri、Rao, Kakulapati Rama、Sattur, Prahlad Balvantrao

  DOI：——

  日期：——