3-methylisoindolo[1,2-b]quinazolin-10(12H)-one | 1182366-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-methylisoindolo[1,2-b]quinazolin-10(12H)-one
• 英文别名: 3-methyl-12H-isoindolo[1,2-b]quinazolin-10-one
• CAS: 1182366-44-4
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: PLRXOSOGAAPERQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 3-methylisoindolo[1,2-b]quinazolin-10(12H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives

  摘要：

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.

  DOI：

  10.1021/ol901305q

文献信息

• Intramolecular Reductive Cyclization of <i>o</i>-Nitroarenes via Biradical Recombination
  作者：Cong Lu、Zhishan Su、Dong Jing、Songyang Jin、Lijuan Xie、Liangrui Li、Ke Zheng

  DOI：10.1021/acs.orglett.9b00191

  日期：2019.3.1

  A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including

  首次实现了在温和条件下可见光诱导的/硫脲介导的邻硝基芳烃分子内环化反应，这为获得药用相关的喹唑啉酮衍生物提供了一种有效且环保的方法。通过使用高效的连续流装置，可以轻松地将反应扩展至克级。包括对照实验，瞬态荧光，紫外可见光谱和DFT计算在内的机理研究表明，通过分子内单电子转移（SET）形成活性双自由基中间体是催化循环的关键阶段。
• Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH₄ )₂ S₂ O₈ -Promoted Intramolecular Oxidative Cyclization
  作者：Lijuan Xie、Cong Lu、Dong Jing、Xinrui Ou、Ke Zheng

  DOI：10.1002/ejoc.201900469

  日期：2019.6.16

  An efficient metal‐free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of fused polycyclic quinazolinone derivatives under mild conditions was disclosed. This method provides an efficient and facile approach to the synthesis of polycyclic quinazolinone derivatives (> 40 examples), as well as the natural products tryptanthrin, rutaecarpine, and their analogues.

  公开了在温和条件下用于构建稠合多环喹唑啉酮衍生物的高效无金属，（NH 4）2 S 2 O 8介导的分子内氧化环化反应。该方法为合成多环喹唑啉酮衍生物（> 40个实例）以及天然产物色胺酮，芸苔芸香碱及其类似物提供了一种高效简便的方法。
• Palladium-catalyzed dicarbonylative synthesis of tetracycle quinazolinones
  作者：Chaoren Shen、Nikki Y. T. Man、Scott Stewart、Xiao-Feng Wu

  DOI：10.1039/c5ob00368g

  日期：——

  An interesting procedure for the synthesis of isoindolo[1,2-b]quinazolin-10(12H)-ones has been developed. Starting from commercially available 2-bromoanilines and 2-bromobenzyl amines, with the assistance of a palladium catalyst, the desired products were isolated in good yields. Notably, this procedure proceeded in a highly selective manner; two molecules of CO were incorporated into the substrates

  已经开发了一种有趣的合成异吲哚并[1,2 - b ]喹唑啉-10（12 H）-ones的方法。从商业上可获得的2-溴苯胺和2-溴苄基胺开始，在钯催化剂的辅助下，以高收率分离出所需产物。值得注意的是，该程序以高度选择性的方式进行。将两个分子的CO选择性地掺入底物中。
• Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives
  作者：Yi Ju、Feng Liu、Chaozhong Li

  DOI：10.1021/ol901305q

  日期：2009.8.20

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.