4-(4,5-dihydro-1H-imidazol-2-yl)quinoline | 1441928-24-0

• 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: 4-(4,5-dihydro-1H-imidazol-2-yl)quinoline
• 英文别名: 2-(Quinolin-4-yl)imidazoline
• CAS: 1441928-24-0
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: WEDJAMMYSATPGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4,5-dihydro-1H-imidazol-2-yl)quinoline 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 N-benzyl-6-[2-(quinolin-4-yl)-4,5-dihydro-1H-imidazol-1-yl]pyridin-2-amine
  参考文献：
  名称：

  Library of diversely substituted 2-(quinolin-4-yl)imidazolines delivers novel non-cytotoxic antitubercular leads

  摘要：

  A novel library based on quinolin-4-ylimidazoline core was designed to incorporate a general quinoline antimicrobial pharmacophore. A synthesis of the well-characterized library of 36 compounds was achieved using the Pd-catalyzed Buchwald-Hartwig-type imidazoline arylation chemistry developed earlier. Compounds were tested for biological activity and were found to possess no antimalarial activity. However, the library delivered two promising antitubercular leads, which are non-cytotoxic and can be further optimized with respect to antimycobacterial potency.

  DOI：

  10.3109/14756366.2015.1101094
• 作为产物：
  描述：

  4-喹啉甲醛 、 乙二胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到4-(4,5-dihydro-1H-imidazol-2-yl)quinoline
  参考文献：
  名称：

  Library of diversely substituted 2-(quinolin-4-yl)imidazolines delivers novel non-cytotoxic antitubercular leads

  摘要：

  A novel library based on quinolin-4-ylimidazoline core was designed to incorporate a general quinoline antimicrobial pharmacophore. A synthesis of the well-characterized library of 36 compounds was achieved using the Pd-catalyzed Buchwald-Hartwig-type imidazoline arylation chemistry developed earlier. Compounds were tested for biological activity and were found to possess no antimalarial activity. However, the library delivered two promising antitubercular leads, which are non-cytotoxic and can be further optimized with respect to antimycobacterial potency.

  DOI：

  10.3109/14756366.2015.1101094

文献信息

• A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines
  作者：Prashant Mujumdar、Tanja Grkovic、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2013.04.036

  日期：2013.6

  We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores. (C) 2013 Elsevier Ltd. All rights reserved.