6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione | 1448998-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡啶
• 英文名称: 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione
• 英文别名: 6,7-Dichloropyrido[1,2-a]benzimidazole-8,9-dione
• CAS: 1448998-63-7
• 化学式: C₁₁H₄Cl₂N₂O₂
• 分子量: 267.071
• InChiKey: YZSAEAVJJBKBLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 7-chloro-8-hydroxypyrido[1,2-a]benzimidazole-6,9-dione
  参考文献：
  名称：

  A novel method for the synthesis of benzimidazole-based 1,4-quinone derivatives

  摘要：

  An efficient method for the synthesis of 8-hydroxypyrido[1,2-a]benzimidazole-6,9-dione derivatives is described. This approach provides convenient access to hydroxypyrido[1,2-a]benzimidazole-6,9-dione analogs bearing electron withdrawing or electron donating substituents under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.002
• 作为产物：
  描述：

  2-氨基吡啶 、 四氯苯醌 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione
  参考文献：
  名称：

  Synthesis of 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione and its analogues and their reactions with nucleophiles

  摘要：

  Novel 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione derivatives and its analogues were synthesized directly from chloranil and different 2-amino(di)azines without using a catalyst or activation. Further nucleophilic substitution reactions were carried out. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.094

文献信息

• Studies of the Functionalized α-Hydroxy-p-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond
  作者：Anastasija Gaile、Sergey Belyakov、Ramona Dūrena、Ņikita Griščenko、Anzelms Zukuls、Nelli Batenko

  DOI：10.3390/molecules29071613

  日期：——

  studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-p-quinone imine derivatives. Synthesized compounds represent a combination of several structural motifs: a benzimidazole core fused with α-hydroxy-p-quinone imine, which contains a benzamide fragment. X-ray crystallography analysis revealed the formation of dimers linked through OH···O interactions and stabilization

  在这项工作中，研究了 6,7-二氯吡啶[1,2-a]苯并咪唑-8,9-二酮与不同苯并酰肼类化合物之间的反应。C（6） 位点的亲核取代之后是异构化，并导致 α-羟基-对醌亚胺衍生物。合成的化合物代表几种结构基序的组合：苯并咪唑核心与 α-羟基-对醌亚胺融合，其中含有苯甲酰胺片段。X 射线晶体学分析揭示了通过 OH···O 相互作用和强分子内 NH···N 氢键。使用紫外-可见光谱和 1H NMR 滴定实验在溶液中研究质子化/去质子化过程。此外，使用循环伏安法测量研究了 6,7-二氯吡啶[1,2-a]苯并咪唑-8,9-二酮及其 α-羟基-对醌亚胺衍生物作为正极材料的电化学性质。基于 6,7-二氯吡啶[1,2-a]苯并咪唑-8,9-二酮的正极材料可以在水性电解质电池中充当潜在的有效活性电极;但是，需要进一步优化。
• A novel method for the synthesis of benzimidazole-based 1,4-quinone derivatives
  作者：Nelli Batenko、Alisa Kricka、Sergey Belyakov、Baiba Turovska、Raimonds Valters

  DOI：10.1016/j.tetlet.2015.12.002

  日期：2016.1

  An efficient method for the synthesis of 8-hydroxypyrido[1,2-a]benzimidazole-6,9-dione derivatives is described. This approach provides convenient access to hydroxypyrido[1,2-a]benzimidazole-6,9-dione analogs bearing electron withdrawing or electron donating substituents under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione and its analogues and their reactions with nucleophiles
  作者：Nelli Batenko、Sergey Belyakov、Glebs Kiselovs、Raimonds Valters

  DOI：10.1016/j.tetlet.2013.06.094

  日期：2013.8

  Novel 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione derivatives and its analogues were synthesized directly from chloranil and different 2-amino(di)azines without using a catalyst or activation. Further nucleophilic substitution reactions were carried out. (C) 2013 Elsevier Ltd. All rights reserved.