4-methyl-6H-isoindolo[2,1-a]indol-6-one | 1600518-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-methyl-6H-isoindolo[2,1-a]indol-6-one
• 英文别名: 4-Methylisoindolo[2,3-a]indol-6-one
• CAS: 1600518-83-9
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: PQOOBMGYDBXWQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2-bromophenyl)-7-methyl-1H-indole 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 4-methyl-6H-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion

  摘要：

  A novel Pd-catalyzed intramolecular cyclization via tert-butyl isocyanide insertion from 2-(2-bromophenyl)-1H-indoles has been developed, which demonstrates the utility of isocyanides in C-N or C-C bond construction. Treatment of 2-(2-bromophenyl)-1H-indoles with tert-butyl isocyanide affords 6H-isoindolo[2,1-a]indol-6-ones with high efficiency. However, N-methyl or N-Boc protected 2-(2-bromophenyl)-1H-indoles gives indenoindolones in excellent yields under the same condition, which reveals that under the described situation, isocyanides insertion for the formation of C-N bonds is prior to that of C-C bonds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.018

文献信息

• Rhodium-Catalyzed NH-Indole-Directed C–H Carbonylation with Carbon Monoxide: Synthesis of 6<i>H</i>-Isoindolo[2,1-<i>a</i>]indol-6-ones
  作者：Qiufeng Huang、Qingshuai Han、Shurong Fu、Zizhu Yao、Lv Su、Xiaofeng Zhang、Shen Lin、Shengchang Xiang

  DOI：10.1021/acs.joc.6b01200

  日期：2016.12.16

  An efficient synthesis of 6H-isoindolo[2,1-a]indol-6-ones through rhodium-catalyzed NH-indole-directed C–H carbonylation of 2-arylindoles with carbon monoxide has been developed. Preliminary mechanistic studies revealed that this reaction proceeds via N–H bond cleavage and subsequent C–H bond cleavage. Reaction monitoring via ESI-MS was used to support the formation of five-membered rhodacycle species

  通过铑催化一氧化碳2-芳基吲哚的NH-吲哚定向的CH羰基化羰基反应，已开发出6 H-异吲哚并[2,1 - a ]吲哚-6-酮的有效合成方法。初步的机理研究表明，该反应通过NH键断裂和随后的CH键断裂进行。通过ESI-MS进行的反应监测用于支持催化循环中五元罗丹环物种的形成。
• Facile approaches toward the synthesis of 6H-isoindolo[2,1-α]indol-6-ones via palladium-catalyzed carbonylation with carbon monoxide
  作者：Qingshuai Han、Shurong Fu、Xiaofeng Zhang、Shen Lin、Qiufeng Huang

  DOI：10.1016/j.tetlet.2016.07.108

  日期：2016.9

  6H-isoindolo[2,1-α]indol-6-ones were developed. In the first protocol, 6H-isoindolo[2,1-α]indol-6-ones were prepared from 2-(2-iodophenyl)-1H-indoles via palladium-catalyzed intramolecular aminocarbonylation. The second involves intermolecular carbonylation of indoles with iodobenzenes followed by intramolecular cross-dehydrogenative-coupling.

  开发了两种简便的制备6 H-异吲哚并[2,1-α]吲哚-6-的方法。在第一协议，6 ħ -isoindolo并[2,1-α]吲哚-6-酮从2-（2-碘苯基）-1制备ħ通过钯-催化的氨基羰基化的分子内-indoles。第二种涉及吲哚与碘苯的分子间羰基化，然后进行分子内的交叉脱氢偶联。
• Synthesis of 6H-isoindolo[2,1- a ]indol-6-ones via Pd-catalyzed cycloaminocarbonylation of 2 -(1H-indol-2-yl)phenyl tosylates with CO
  作者：Bin Liu、Chunbo Lai、Chunlei Zhang、Xigeng Zhou

  DOI：10.1016/j.tet.2017.12.058

  日期：2018.2

  2-(1H-indol-2-yl)benzamides are formed when an excess of amine is used in this reaction system. Alternatively, 2-(1H-indol-2-yl)benzamides can also be synthesized by the in situ aminolysis of 2. Furthermore, treatment of 2 with hydrosilane in the presence of KOH gave the unprecedented reducing products 2-(-1H-indol-2-yl)benzyl alcohols in 75–86% yields. These results demonstrate that 6H-isoindolo[2

  钯催化开发了一种有效的制备取代的6H-异吲哚并[ 2,1 - a ]吲哚-6-酮（2）的有效方法，该取代的6H-isoindolo [ 2,1 - a ]吲哚-6-酮是大量天然存在的药理活性化合物的重要结构组分。的分子内cycloaminocarbonylation 2 - （1H-吲哚-2-基）苯基甲苯磺酸酯用CO值得注意的是，分子间氨基羰基化产物2 - （1H-吲哚-2-基）当过量的胺在该反应系统中使用形成的苯甲酰胺的。或者，还可以通过2的原位氨解来合成2-（1H-吲哚-2-基）苯甲酰胺。而且，治疗2在KOH的存在下与氢硅烷反应，以75-86％的收率得到了空前的还原产物2 -（-1H-吲哚-2-基）苄醇。这些结果证明6H-异吲哚并[2，1- a ]吲哚-6-酮是用于进一步合成加工的通用底物。
• Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids
  作者：Hirotsugu Suzuki、Takanori Matsuda、Yosuke Takemura

  DOI：10.1055/a-2278-5797

  日期：2024.10

  We developed a redox-neutral synthesis of isoindoloindolone via intramolecular arylation of 2-(1H-indole-1-carbonyl)benzoic acids. This protocol facilitates the formation of various substituted isoindoloindolones in yields ranging from 17% to 80%. Our mechanistic investigations indicate the pivotal role of NaI: the iodide anion promotes the formation of the desired isoindoloindolone, and the sodium

  我们通过 2-(1 H-吲哚-1-羰基)苯甲酸的分子内芳基化开发了异吲哚并吲哚酮的氧化还原中性合成。该方案促进了各种取代异吲哚并吲哚酮的形成，产率范围为 17% 至 80%。我们的机理研究表明 NaI 的关键作用：碘化物阴离子促进所需异吲哚并吲哚酮的形成，钠阳离子抑制酰化副产物的形成，从而能够以可接受的产率选择性形成异吲哚并吲哚酮。
• Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones via Palladium-Catalyzed Carbonylative Cyclization of 2-(2-Bromophenyl)-1H-indoles
  作者：Chan Cho、Jae Yoo、Son Ho

  DOI：10.1055/s-0035-1561560

  日期：——

  2-(2-Bromophenyl)-1H-indoles are carbonylatively cyclized under carbon monoxide pressure in toluene in the presence of a catalytic amount of PdCl2 and PPh3 along with a base to give 6H-isoindolo[2,1-a]indol-6-ones in high yields.