9-methylbenzo[4,5]imidazo[1,2-a]pyridine | 474537-07-0

• 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: 9-methylbenzo[4,5]imidazo[1,2-a]pyridine
• 英文别名: 9-methylpyrido[1,2-a]benzimidazole
• CAS: 474537-07-0
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: QHUVTICLUMPEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 9-methylbenzo[4,5]imidazo[1,2-a]pyridine 以 乙腈 为溶剂， 生成 5-ethyl-9-methylpyrido[1,2-a]benzimidazolium iodide
  参考文献：
  名称：

  摘要：

  Photocyclization of 2-(pentafluoroanilino)-, 2-(4-chloro-2-iodoanilino)-, and 2-(2-chloro-4-iodoanitino)-4,6-dimethylpyrimidines, as well as 2-(2-chloro-3-methylanilino)pyridine was used to prepare condensed azinobenzimidazoles, including previously unknown 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole and 9-methylpyrido[1,2-a]benzimidazole. With isomeric chloroiodoanilinopyrimidines as example it was shown that the iodine atom affects photocyclization direction. Quaternization of 6,7,8,9-tetrafluoro-1,3-dimethylpyrimido [ 1,2-a]benzimidazole, 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole, and 9-methylpyrido[1,2-a]benzimidazole with alkylating agents and C-H activity of alkyl groups in the quaternary salts in reactions with orthoformic ester were studied.

  DOI：

  10.1023/a:1015420423421
• 作为产物：
  描述：

  2-氯-3-甲基苯胺 以 phosphate buffer 、 叔丁醇 为溶剂， 反应 15.0h， 生成 9-methylbenzo[4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  摘要：

  Photocyclization of 2-(pentafluoroanilino)-, 2-(4-chloro-2-iodoanilino)-, and 2-(2-chloro-4-iodoanitino)-4,6-dimethylpyrimidines, as well as 2-(2-chloro-3-methylanilino)pyridine was used to prepare condensed azinobenzimidazoles, including previously unknown 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole and 9-methylpyrido[1,2-a]benzimidazole. With isomeric chloroiodoanilinopyrimidines as example it was shown that the iodine atom affects photocyclization direction. Quaternization of 6,7,8,9-tetrafluoro-1,3-dimethylpyrimido [ 1,2-a]benzimidazole, 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole, and 9-methylpyrido[1,2-a]benzimidazole with alkylating agents and C-H activity of alkyl groups in the quaternary salts in reactions with orthoformic ester were studied.

  DOI：

  10.1023/a:1015420423421

文献信息

• A Metal-Free Tandem Demethylenation/C(sp²)–H Cycloamination Process of <i>N</i>-Benzyl-2-aminopyridines via C–C and C–N Bond Cleavage
  作者：Dongdong Liang、Yimiao He、Lanying Liu、Qiang Zhu

  DOI：10.1021/ol4015656

  日期：2013.7.5

  A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C–C and C–N bond cleavage.

  已经开发了一种轻度，无金属的合成方法，该方法以N-苄基-2-氨基吡啶为原料，以PhI（OPiv）2为化学计量氧化剂，合成了吡啶并[1,2- a ]苯并咪唑类化合物。该过程由一个不寻常的岛（OPiv）发起2介导的本位小号ë的Ar反应，接着进行溶剂辅助C-C和C-N键断裂。
• Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions
  作者：Yanjun Xie、Jun Wu、Xingzong Che、Ya Chen、Huawen Huang、Guo-Jun Deng

  DOI：10.1039/c5gc01978h

  日期：——

  Pyrido[1,2-a]benzimidazole derivatives were selectively prepared from 2-aminopyridines and cyclohexanones under metal free conditions.

  通过无金属条件下，从2-氨基吡啶和环己酮选择性地制备了吡啶并咪唑衍生物。
• ——
  作者：A. N. Frolov

  DOI：10.1023/a:1015420423421

  日期：——

  Photocyclization of 2-(pentafluoroanilino)-, 2-(4-chloro-2-iodoanilino)-, and 2-(2-chloro-4-iodoanitino)-4,6-dimethylpyrimidines, as well as 2-(2-chloro-3-methylanilino)pyridine was used to prepare condensed azinobenzimidazoles, including previously unknown 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole and 9-methylpyrido[1,2-a]benzimidazole. With isomeric chloroiodoanilinopyrimidines as example it was shown that the iodine atom affects photocyclization direction. Quaternization of 6,7,8,9-tetrafluoro-1,3-dimethylpyrimido [ 1,2-a]benzimidazole, 8-chloro-1,3-dimethylpyrimido[1,2-a]benzimidazole, and 9-methylpyrido[1,2-a]benzimidazole with alkylating agents and C-H activity of alkyl groups in the quaternary salts in reactions with orthoformic ester were studied.