6-(thiophen-2-yl)benzo[4,5]imidazo[2,1-a]isoquinoline | 1417819-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(thiophen-2-yl)benzo[4,5]imidazo[2,1-a]isoquinoline
• 英文别名: 6-Thiophen-2-ylbenzimidazolo[2,1-a]isoquinoline；6-thiophen-2-ylbenzimidazolo[2,1-a]isoquinoline
• CAS: 1417819-37-4
• 化学式: C₁₉H₁₂N₂S
• 分子量: 300.384
• InChiKey: SCEVKVDRHMVSRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 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：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

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38 mg的产率得到6-(thiophen-2-yl)benzo[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

• 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。
• Selective one-pot synthesis of 11-arylmethylidene-11 H -isoindolo-[2,1- a ]benzimidazoles and 6-arylbenzimidazo[2,1- a ]isoquinolines from o -alkynylbenzaldehydes and o -diaminobenzenes
  作者：Valentin D. Gvozdev、Konstantin N. Shavrin、Esfir G. Baskir、Mikhail P. Egorov、Oleg M. Nefedov

  DOI：10.1016/j.mencom.2017.05.004

  日期：2017.5

  Cyclization of o-alkynylbenzaldehydes with o-diamino-benzenes in DMSO under the sequential action of NH4Br and K2CO3 affords 11-arylmethylidene-11H-isoindolo[2,1-a]benzimidazoles as a result of 5-exo-dig ring closure; whereas replacement of treating with K2CO3 by heating at 110-115 degrees C results in 6-endo-dig cyclization with formation of 6-aryl-benzimidazo[2,1-a]isoquinolines.
• 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.