6,7-dichloro-2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitrile | 1449576-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6,7-dichloro-2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitrile
• 英文别名: 6,7-dichloro-2-phenyl-1H-imidazo[4,5-b]quinoline-9-carbonitrile
• CAS: 1449576-70-8
• 化学式: C₁₇H₈Cl₂N₄
• 分子量: 339.183
• InChiKey: PTUMLHTWFYCFPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3,4-二氯苯基)苯甲脒 以 四氢呋喃 、 甲醇 、 二苯醚 为溶剂， 反应 9.0h， 生成 6,7-dichloro-2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitrile 、 7,8-dichloro-2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitrile
  参考文献：
  名称：

  Reactions of Tetracyanoethylene with N′-Arylbenzamidines: A Route to 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles

  摘要：

  Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N'-arylbenzamidines 11 and tetracyanoethylene (TCNE) in similar to 70-90% yields. The transformation involves the initial formation of N-aryl-N'-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles 13 in 84-92% yields, while in MeOH the (Z)-2[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85-94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations.

  DOI：

  10.1021/jo4013699