5-methyl-benzo[4,5]imidazo[1,2-a]quinoline | 129815-55-0

• 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: 5-methyl-benzo[4,5]imidazo[1,2-a]quinoline
• 英文别名: 5-methylquino<1,2-a>benzimidazole；5-methylquinolino[1,2-a]benzimidazole；5-Methylquino[1,2-a]benzimidazole；5-methylbenzimidazolo[1,2-a]quinoline
• CAS: 129815-55-0
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: VPBZGPHGDZYQDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  5-methyl-benzo[4,5]imidazo[1,2-a]quinoline 、 碘乙烷 以 乙腈 为溶剂， 生成 7-ethyl-5-methylquinolino[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-(2-chloroanilino)-4-methylquinoline 在 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以0.34 g的产率得到5-methyl-benzo[4,5]imidazo[1,2-a]quinoline
  参考文献：
  名称：

  Baklanov, M. V.; Frolov, A. N., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 5.2, p. 983 - 984

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Intramolecular N-Arylation of Heteroarenes:  A Novel and Efficient Route to Benzimidazo[1,2-<i>a</i>]quinolines
  作者：C. Venkatesh、G. S. M. Sundaram、H. Ila、H. Junjappa

  DOI：10.1021/jo0522411

  日期：2006.2.1

  An efficient new route for the synthesis of benzimidazo[1,2-a]quinolines has been developed via the palladium-catalyzed intramolecular Buchwald−Harwtig aryl amination of newly synthesized 2-(2‘-bromoanilino)quinolines.

  通过钯催化的新合成的2-（2'-溴苯胺基）喹啉的分子内布赫瓦尔德-哈瓦提芳基胺化反应，已开发出一种合成苯并咪唑并[1,2- a ]喹啉的有效新途径。
• BAKLANOV, M. V.;FROLOV, A. N., ZH. ORGAN. XIMII, 25,(1990) N, S. 1141-1142
  作者：BAKLANOV, M. V.、FROLOV, A. N.

  DOI：——

  日期：——
• BAKLANOV, M. V.;FROLOV, A. N., ZH. ORGAN. XIMII, 27,(1991) N, S. 638-649
  作者：BAKLANOV, M. V.、FROLOV, A. N.

  DOI：——

  日期：——
• ——
  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.
• Baklanov, M. V.; Frolov, A. N., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 5.2, p. 983 - 984
  作者：Baklanov, M. V.、Frolov, A. N.

  DOI：——

  日期：——