3-chloro-13H-indolo[3,2-c]acridine

• 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: 3-chloro-13H-indolo[3,2-c]acridine
• 化学式: C₁₉H₁₁ClN₂
• 分子量: 302.763
• InChiKey: ARWBZEXIFRXFRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-chloro-6,13-dihydro-5H-indolo[3,2-c]acridine-7-carboxylic acid 在 5% Pd(II)/C(eggshell) 作用下， 以 二苯醚 为溶剂， 反应 4.0h， 以60%的产率得到3-chloro-13H-indolo[3,2-c]acridine
  参考文献：
  名称：

  Simple and Convenient Methods for the Synthesis of Indolo[3,2-c]acridines

  摘要：

  The reaction of 2,3,4,9-tetrahydro-1H-carbazol-1-ones with anthranilic acid in POCl3 yielded 7-chloro-5,6-dihydro-13H-indolo[3,2-c]acridines, while the same on reaction with isatin under the Pfitzinger reaction condition yielded 5,6-dihydro-13H-indolo[3,2-c]acridine-7-carboxylic acids. The latter reaction was carried out in different basic condition, because of, NaOH yielded more yield instead of KOH. Both the obtained products were treated with Pd/C in diphenyl ether to yield 13H-Indolo[3,2-c]acridines.

  DOI：

  10.1080/00397910903457365

文献信息

• Novel 13H-indolo[3,2-c]acridines and Their Methyl Derivatives
  作者：Makuteswaran Sridharan、Karnam Jayarampillai Rajendra Prasad

  DOI：10.3184/030823407x198410

  日期：2007.3

  7-Phenyl-13H-indolo[3,2-c]acridines (2a–e) have been prepared from 2,3,4,9-tetrahydro-1H-carbazol-1-ones (1a–e) via the intermediate 5,6-dihydro-derivatives (3a–e), and 13H-indolo[3,2-c]acridines (8a–e) from the 1-(N-phenylamino)carbazoles (7a–e). Methylations of 2 and 8 have been carried out, and UV spectral studies on the title compounds and the methylated products are presented, along with plausible mechanisms for the formation of the final compounds.

  通过中间体 5,6-二氢衍生物 (3a-e) 从 2,3,4,9-四氢-1H-咔唑-1-酮 (1a-e) 中制备出 7-苯基-13H-吲哚并[3,2-c]吖啶 (2a-e)，并通过 1-(N-苯基氨基)咔唑 (7a-e) 从 13H-吲哚并[3,2-c]吖啶 (8a-e) 中制备出 13H-吲哚并[3,2-c]吖啶 (8a-e)。对 2 和 8 进行了甲基化，并对标题化合物和甲基化产物进行了紫外光谱研究，同时还介绍了最终化合物的合理形成机制。
• Simple and Convenient Methods for the Synthesis of Indolo[3,2-<i>c</i>]acridines
  作者：Kumaresan Prabakaran、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1080/00397910903457365

  日期：2010.11.3

  The reaction of 2,3,4,9-tetrahydro-1H-carbazol-1-ones with anthranilic acid in POCl3 yielded 7-chloro-5,6-dihydro-13H-indolo[3,2-c]acridines, while the same on reaction with isatin under the Pfitzinger reaction condition yielded 5,6-dihydro-13H-indolo[3,2-c]acridine-7-carboxylic acids. The latter reaction was carried out in different basic condition, because of, NaOH yielded more yield instead of KOH. Both the obtained products were treated with Pd/C in diphenyl ether to yield 13H-Indolo[3,2-c]acridines.