6-(2-methoxyphenyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione

• 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: 6-(2-methoxyphenyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
• 英文别名: 6-(2-methoxyphenyl)-6aH-isoindolo[2,3-a]quinazoline-5,11-dione
• 化学式: C₂₂H₁₆N₂O₃
• 分子量: 356.381
• InChiKey: WDNVUZIOHZOCOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴苯酞 、 靛红酸酐 、 邻甲氧基苯胺 在 PEG-400 作用下， 以 水 为溶剂， 以71%的产率得到6-(2-methoxyphenyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
  参考文献：
  名称：

  Metal–Catalyst-Free Green and efficient synthesis of five and six membered fused N-heterocyclic quinazoline derivatives

  摘要：

  An efficient and green approach has been developed for the construction of Tetracyclic nitrogen-bridgehead compounds were designed and synthesized in good yields. The reaction of easily prepared 3-bromoisobenzofuran-1(3H)-one with isatoic anhydride and amines gave the desired isoindoloquinazolinone derivatives in moderate to good yields. It is also amenable for scale-up. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.09.094

文献信息

• Wang-OSO3H catalyzed green synthesis of bioactive isoindolo[2,1-a]quinazoline-5,11‑dione derivatives: An unexpected observation
  作者：G Dhananjaya、Rapolu Venkateshwarlu、Naresh Kumar Reddy Dinne、Avula Mahesh Kumar、Ramamohan Mekala、Venkateswara Rao Anna、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1016/j.molstruc.2021.131922

  日期：2022.2

  acidic catalyst for the synthesis of isoindolo[2,1-a]quinazoline-5,11-dione derivatives under green conditions. Thus the Wang-OSO3H catalyzed MCR of isatoic anhydride, 2-formylbenzoic acid and various amines in pure water afforded a range of desired product in good to excellent (86-94%) yield. The methodology can be performed under open air and is amenable for scale-up synthesis. The catalyst can be recovered

  磺酸官能化的 Wang 树脂 (Wang-OSO 3 H) 被探索作为一种聚合和可回收的酸性催化剂，用于在绿色条件下合成异吲哚并 [ 2,1- a ] 喹唑啉-5,11-二酮衍生物。因此，Wang-OSO 3H 催化的靛红酸酐、2-甲酰基苯甲酸和各种胺在纯水中的 MCR 以良好至极好的 (86-94%) 产率提供了一系列所需产物。该方法可以在露天下进行，并且适合放大合成。催化剂可多次回收和循环使用，其催化活性没有明显损失。在一种情况下观察到的 2-(1-羟基-3-氧代异吲哚啉-2-基)苯甲酰胺衍生物的意外形成可能允许通过使用适当的胺从相同的 MCR 获得此类杂环。计算机评估表明，已知的 TNF-α 抑制剂化合物4j可能是 SARS-CoV-2 的潜在配体，它通过其 OMe 和两个 C=O 基团与其形成 H 键。
• Metal–Catalyst-Free Green and efficient synthesis of five and six membered fused N-heterocyclic quinazoline derivatives
  作者：M.V. Madhubabu、R. Shankar、G. Rajeshwar Reddy、T. Srinivasa Rao、Mandava V. Basaveswara Rao、Raghunadh Akula

  DOI：10.1016/j.tetlet.2016.09.094

  日期：2016.11

  An efficient and green approach has been developed for the construction of Tetracyclic nitrogen-bridgehead compounds were designed and synthesized in good yields. The reaction of easily prepared 3-bromoisobenzofuran-1(3H)-one with isatoic anhydride and amines gave the desired isoindoloquinazolinone derivatives in moderate to good yields. It is also amenable for scale-up. (C) 2016 Elsevier Ltd. All rights reserved.