9-chloro-6-phenyl-1,2,5,6-tetrahydrobenzo[b]imidazo[1,2,3-ij]-[1,8]naphthyridine-4,7-dione | 1256151-10-6

• 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: 9-chloro-6-phenyl-1,2,5,6-tetrahydrobenzo[b]imidazo[1,2,3-ij]-[1,8]naphthyridine-4,7-dione
• 英文别名: 5-Chloro-10-phenyl-1,13-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-2(7),3,5,9(16)-tetraene-8,12-dione
• CAS: 1256151-10-6
• 化学式: C₂₀H₁₅ClN₂O₂
• 分子量: 350.804
• InChiKey: DKXZHLPCNWJZAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 9-chloro-6-phenyl-1,2,5,6-tetrahydrobenzo[b]imidazo[1,2,3-ij]-[1,8]naphthyridine-4,7-dione
  参考文献：
  名称：

  Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-ij][1,8]naphthyridines

  摘要：

  Two new kinds of tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyndine derivatives have been successfully synthesized by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomenzation, cyclocondensation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines with aromatic aldehydes and ethyl acetoacetate or Meldrum's acid under mild conditions, respectively These studies highlighted the concept of a substrate-design approach to the development of novel multicomponent reactions by simply incorporating an o-halo group into the aryl ring of 2-benzoyl-methyleneimidazolidine as new synthons In this domino reaction, at least six different active sites are involved, two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation

  DOI：

  10.1021/jo101454q

文献信息

• A facile synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines through NHC-catalyzed cascade annulations
  作者：Changsheng Yao、Weihui Jiao、Zhaoxin Xiao、Yuanwei Xie、Tuanjie Li、Xiangshan Wang、Rui Liu、Chenxia Yu

  DOI：10.1039/c3ra41935e

  日期：——

  A new efficient approach for the synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydrobenzo[b]imidazo[1,2,3-ij][1,8]naphthyridines with biological significance was successfully developed through a NHC-catalyzed cascade C–C bond and C–N bond formation process. This new alternative approach for the assembly of these multi-functionalized nitrogen bridgehead-fused heterocycles features mild conditions

  通过NHC催化的级联反应成功开发了一种新的高效合成四氢咪唑并[1,2- a ]吡啶和四氢苯并[ b ]咪唑并[1,2,3- ij ] [1,8]萘啶的新方法C–C键和C–N键的形成过程。组装这些多功能氮桥头稠合杂环的这种新的替代方法具有温和的条件，中等至高收率和操作简便性。
• Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR: Selective Construction of Tetrahydrobenzo[<i>b</i>]imidazo[3,2,1-<i>ij</i>][1,8]naphthyridines
  作者：Li-Rong Wen、Chao Liu、Ming Li、Li-Juan Wang

  DOI：10.1021/jo101454q

  日期：2010.11.19

  Two new kinds of tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyndine derivatives have been successfully synthesized by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomenzation, cyclocondensation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines with aromatic aldehydes and ethyl acetoacetate or Meldrum's acid under mild conditions, respectively These studies highlighted the concept of a substrate-design approach to the development of novel multicomponent reactions by simply incorporating an o-halo group into the aryl ring of 2-benzoyl-methyleneimidazolidine as new synthons In this domino reaction, at least six different active sites are involved, two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation