2-(2-bromopyridin-3-yl)-1H-benzo[d]imidazole | 1246929-38-3

• 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: 2-(2-bromopyridin-3-yl)-1H-benzo[d]imidazole
• 英文别名: 2-(2-bromopyridin-3-yl)-1H-benzimidazole
• CAS: 1246929-38-3
• 化学式: C₁₂H₈BrN₃
• 分子量: 274.12
• InChiKey: RIJXAOCOKOYZDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-(2-bromopyridin-3-yl)-1H-benzo[d]imidazole 、 3-溴丙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以95%的产率得到1-allyl-2-(2-bromopyridin-3-yl)-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents

  摘要：

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.025
• 作为产物：
  描述：

  2-溴-3-吡啶甲醛 、 邻苯二胺 在 sodium hydrogensulfite 作用下， 以 水 为溶剂， 生成 2-(2-bromopyridin-3-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  苯并咪唑和咪唑并菲啶骨架的串联钯/铜催化脱羧方法

  摘要：

  介绍了邻溴苯甲酸和 2-(2-溴芳基)-1 H-苯并 [ d ] 咪唑或相应咪唑之间串联 Pd/Cu 催化分子间交叉偶联级联的方案。该协议提供了概念上新颖且可控的途径，可用于合成有用的N-融合（苯并）咪唑并菲啶支架，具有高效率、广泛的底物范围和出色的官能团相容性。

  DOI：

  10.1021/acs.orglett.2c03647

文献信息

• Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents
  作者：Eoin Moriarty、Miriam Carr、Sarah Bonham、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1016/j.ejmech.2010.05.025

  日期：2010.9

  A facile 6-exo-trig cyclization of sigma-aromatic radicals has allowed the synthesis of various aromatic ring fused benzimidazoles and benzimidazolequinones. The most highly conjugated naphthyl fused benzimidazolequinone, (5-methyl-5,6-dihydrobenzimidazo[2,1-a]benzo[f]isoquinoline-8,11-dione) showed the highest specificity towards human cervical (HeLa) and prostate (DU145) cancer cell lines with little toxicity towards a human normal (GM00637) cell line at doses of <1 mu M. In contrast, 2-aromatic ring substituted (benzimidazole-4,7-diones) analogues, benzimidazolequinone with a pyridine ring and mitomycin C were more toxic than the highly conjugated naphthyl fused benzimidazolequinone towards the normal cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Tandem Palladium/Copper-Catalyzed Decarboxylative Approach to Benzoimidazo- and Imidazophenanthridine Skeletons
  作者：Xin Geng、Andrey Shatskiy、Gregory R. Alvey、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.orglett.2c03647

  日期：2022.12.23

  A protocol for a tandem Pd/Cu-catalyzed intermolecular cross-coupling cascade between o-bromobenzoic acids and 2-(2-bromoaryl)-1H-benzo[d]imidazoles or the corresponding imidazoles is presented. The protocol provides conceptually novel and controlled access to synthetically useful N-fused (benzo)imidazophenanthridine scaffolds with high efficiency, a broad substrate scope, and excellent functional

  介绍了邻溴苯甲酸和 2-(2-溴芳基)-1 H-苯并 [ d ] 咪唑或相应咪唑之间串联 Pd/Cu 催化分子间交叉偶联级联的方案。该协议提供了概念上新颖且可控的途径，可用于合成有用的N-融合（苯并）咪唑并菲啶支架，具有高效率、广泛的底物范围和出色的官能团相容性。