3-chloro-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline | 1417818-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-chloro-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline
• 英文别名: 3-Chloro-6-phenylbenzimidazolo[2,1-a]isoquinoline；3-chloro-6-phenylbenzimidazolo[2,1-a]isoquinoline
• CAS: 1417818-96-2
• 化学式: C₂₁H₁₃ClN₂
• 分子量: 328.801
• InChiKey: XMNQKJJMACAZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  在 palladium diacetate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以30 mg的产率得到3-chloro-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline
  参考文献：
  名称：

  Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines

  摘要：

  An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.

  DOI：

  10.1021/jo302471z

文献信息

• An efficient synthesis of 6-arylbenzo[4,5]imidazo[2,1-a]isoquinolines via sequential α-arylation of carbonyl and deacylation catalyzed by CuI
  作者：Wei-Qing Miao、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1039/c7ob01022b

  日期：——

  Dibenzoyl methane was found to undergo α-arylation of carbonyl and deacylation reaction with 2-(2-bromophenyl)-1H-benzo[d]imidazoles catalyzed by CuI in the presence of Cs2CO3, and provided an efficient synthesis of 6-arylbenzo[4,5]imidazo[2,1-a]isoquinolines via subsequent intra-molecular nucleophilic addition and dehydration.

  发现二苯甲酰甲烷在Cs 2 CO 3存在下与CuI催化的2-（2-溴苯基）-1 H-苯并[ d ]咪唑发生羰基的α-芳基化反应和脱酰反应，并有效合成了6 -芳基苯并[4,5]咪唑并[2,1- a ]异喹啉通过随后的分子内亲核加成和脱水作用。
• Rhodium-Catalyzed Annulation of 2-Arylimidazoles and α-Aroyl Sulfoxonium Ylides toward 5-Arylimidazo[2,1-a]isoquinolines
  作者：Jiang Cheng、Rui Yang、Xiaopeng Wu、Song Sun、Jin-Tao Yu

  DOI：10.1055/s-0037-1610124

  日期：2018.9

  A Rh-catalyzed annulation between 2-aryl-1H-benzo[d]imidazoles and α-aroyl sulfoxonium ylides was developed, affording a series of benzimidazo[2,1-a]isoquinolines in moderate to excellent yields. This procedure proceeded with the sequential ortho-C–H functionalization and cyclization, representing a facile and straightforward pathway to access such frameworks.

  开发了一种Rh催化的2-芳基-1H-苯并[d]咪唑和α-酰基亚磺酸盐叶立德之间的环化反应，产率中等至优异，得到了一系列苯并咪唑[2,1-a]异喹啉。该过程采用顺序的ortho-C-H官能团化和环化反应，是一种简单直接的途径来获得这种骨架。
• Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolines
  作者：Jinsong Peng、Guoning Shang、Chunxia Chen、Zhongshuo Miao、Bin Li

  DOI：10.1021/jo302471z

  日期：2013.2.1

  An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.