benzo[4',5']imidazo[1',2':1,4]azeto[2,3-b]quinoline | 1610807-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶二氮卓类
• 英文名称: benzo[4',5']imidazo[1',2':1,4]azeto[2,3-b]quinoline
• 英文别名: 2,9,19-Triazapentacyclo[9.8.0.02,10.03,8.013,18]nonadeca-1(19),3,5,7,9,11,13,15,17-nonaene；2,9,19-triazapentacyclo[9.8.0.02,10.03,8.013,18]nonadeca-1(19),3,5,7,9,11,13,15,17-nonaene
• CAS: 1610807-03-8
• 化学式: C₁₆H₉N₃
• 分子量: 243.268
• InChiKey: CAKWYSWGZGFITF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(1H-benzo[d]imidazol-2-yl)-2-chloroquinoline 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 10.0h， 生成 benzo[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

文献信息

• One-Pot Synthesis of Novel Quinoline-Fused Azeto[1,2-a]benzimidazole Analogs Via Intramolecular Pd-Catalyzed C–N Coupling
  作者：Amit B. Patel、Premlata Kumari、Kishor H. Chikhalia

  DOI：10.1007/s10562-014-1266-9

  日期：2014.7

  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.