7-chloro-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine | 18443-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-chloro-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine
• 英文别名: 7-Chlor-1,2,3,4-tetrahydro-pyrido<1,2-a>benzimidazol；7-Chloro-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole
• CAS: 18443-20-4
• 化学式: C₁₁H₁₁ClN₂
• 分子量: 206.675
• InChiKey: MHVVQHLBAPDDOT-UHFFFAOYSA-N

物化性质

• 沸点：
  396.4±15.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-chloro-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 titanium(III) chloride 、 硫酸 、 potassium nitrate 作用下， 以 水 、 异丙醇 为溶剂， 反应 19.0h， 生成 8-bromo-7-chloro-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole-6,9-dione
  参考文献：
  名称：

  Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen

  摘要：

  A facile synthesis ofpara-quinones derived from fused benzimidazoles with a bridgehead nitrogen atom was developed. The heterocyclic quinone core formed as a result of reductive cyclization ofortho-nitroarenes containing alicyclic and aromatic azaheterocycles. Functionalization of 1,2,3,4-tetrahydro- and pyrido[1,2-a]benzimidazoles viaS(E)Ar, condensation, and reduction reactions allowed synthesis of amino derivatives which were oxidized with KNO(3)in H(2)SO(4)to obtain novel heterocyclic quinones.

  DOI：

  10.1134/s1070428020080084
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 sodium azide 、 sodium acetate 作用下， 生成 7-chloro-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  吡啶和哌啶-（1'：2'-1：2）苯并咪唑系列的合成

  摘要：

  DOI：

  10.1039/jr9550003275

文献信息

• Formic acid as a sustainable and complementary reductant: an approach to fused benzimidazoles by molecular iodine-catalyzed reductive redox cyclization of o-nitro-t-anilines
  作者：T. B. Nguyen、L. Ermolenko、A. Al-Mourabit

  DOI：10.1039/c6gc00902f

  日期：——

  Molecular iodine was found to be an excellent catalyst for reductive redox cyclization ofo-nitro-t-anilines1into fused tricyclic or 1,2-disubtituted benzimidazoles2.

  分子碘被发现是一种优秀的催化剂，可用于将o-硝基-t-苯胺还原氧化环化成融合的三环或1,2-二取代苯并咪唑。
• Metal-free construction of tricyclic or tetracyclic compounds—acid-promoted synthesis of benzo[4,5]imidazo[2,1-a]isoindole and 1,2-dialkyl-2,3-dihydrobenzimidazoles
  作者：Jinying Chen、Jinpeng Qu、Yuanqing Zhang、Yongxin Chen、Na Liu、Baohua Chen

  DOI：10.1016/j.tet.2012.10.030

  日期：2013.1

  An environmental friendly, efficient, and easy to operate strategy for synthesizing of benzo[4,5]imidazo [2,1-a]isoindole and 1,2-dialkyl-2,3-dihydrobenzimidazoles via acid-promoted coupling of dialdehyde and o-diaminobenzene under metal-free conditions is described. A series of products were generated in good yields under mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• Electroreductive heterocyclization of ortho-piperidino substituted nitro(het)arenes
  作者：Roman S. Begunov、Valeria O. Sakulina、Mikhail A. Syroeshkin、Evgeniya A. Saverina、Alexandr A. Sokolov、Mikhail E. Minyaev

  DOI：10.1016/j.mencom.2020.09.027

  日期：2020.9

  Electrochemical reduction of ortho-piperidino substituted nitro(het)arenes in an undivided cell on a lead cathode in 8% HCl gave either 1,2,3,4-tetrahydropyrido[1,2-a]-benzimidazoles or 6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]-pyridines. The reductive heterocyclization mechanism involves the initial formation of a nitroso derivative followed by the formation of an imidazole ring.
• Syntheses in the pyrido- and piperido-(1′ : 2′-1 : 2)benziminazole series
  作者：K. H. Saunders

  DOI：10.1039/jr9550003275

  日期：——
• Synthesis of Quinone Derivatives of Benzannelated Heterocycles with Bridgehead Nitrogen
  作者：R. S. Begunov、A. A. Sokolov、S. I. Filimonov

  DOI：10.1134/s1070428020080084

  日期：2020.8

  A facile synthesis ofpara-quinones derived from fused benzimidazoles with a bridgehead nitrogen atom was developed. The heterocyclic quinone core formed as a result of reductive cyclization ofortho-nitroarenes containing alicyclic and aromatic azaheterocycles. Functionalization of 1,2,3,4-tetrahydro- and pyrido[1,2-a]benzimidazoles viaS(E)Ar, condensation, and reduction reactions allowed synthesis of amino derivatives which were oxidized with KNO(3)in H(2)SO(4)to obtain novel heterocyclic quinones.