6-phenyl-5,6-dihydro-8H-quinazolino[4,3-b]quinazolin-8-one | 73565-06-7

• 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-phenyl-5,6-dihydro-8H-quinazolino[4,3-b]quinazolin-8-one
• 英文别名: 6-phenyl-5H-quinazolino[4,3-b]quinazolin-8(6H)-one；6-phenyl-5,6-dihydroquinazolino[4,3-b]quinazolin-8-one
• CAS: 73565-06-7
• 化学式: C₂₁H₁₅N₃O
• 分子量: 325.37
• InChiKey: YFBZISVUBFEIAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phenyl-5,6-dihydro-8H-quinazolino[4,3-b]quinazolin-8-one 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 20.0h， 生成 6-phenyl-8H-quinazolino[4,3-b]quinazolin-8-one
  参考文献：
  名称：

  Rao, C. V. Chalapathi; Reddy, K. Kondal; Rao, N. V. Subba, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 8, p. 655 - 658

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯甲醛 在 copper(II) choride dihydrate 、 水 、 铁粉 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 28.0h， 生成 6-phenyl-5,6-dihydro-8H-quinazolino[4,3-b]quinazolin-8-one
  参考文献：
  名称：

  醛驱动、Fe(0) 介导的一锅还原环化：直接获得 5,6-二氢-喹唑啉并[4,3-b]喹唑啉-8-酮和光物理研究

  摘要：

  通过 Fe(0) 粉末介导的一锅还原环化方案，揭示了双杂环5,6-二氢-喹唑啉代[4,3- b ]喹唑啉-8-酮的简短、高效和区域选择性合成。机理研究证明，水作为硝基还原的氢源，醛加速了反应速率。设计的转化在有氧条件下进行，提供了一系列仿生分子支架。此外，光物理研究表明蓝色荧光发射具有良好的荧光量子产率。

  DOI：

  10.1021/acs.joc.3c00766

文献信息

• Synthesis of 6-aryl-5H-quinazolino[4,3-b]quinazolin-8(6H)-one derivatives in ionic liquids catalyzed by iodine
  作者：Yong-Gang Ma、Yan Zhang、Bin-Bin Feng、Xiang-Shan Wang

  DOI：10.1007/s11164-015-2072-8

  日期：2016.2

  Abstract The iodine-catalyzed reaction of 2-(2-aminophenyl)quinazolin-4(3 H )-ones and benzaldehydes was treated in ionic liquids, giving a series of 6-aryl-5 H -quinazolino[4,3- b ]quinazolin-8(6 H )-one derivatives in high yields. This novel procedure has the advantages of high yields, being metal-free and having a mild reaction condition. Graphical Abstract

  摘要在离子液体中处理 了2-（2-氨基苯基）喹唑啉-4（3 H ）-酮与苯甲醛的碘催化反应 ，得到了一系列6-芳基-5 H- 喹唑啉代[4,3- b ]。高产率的喹唑啉-8（6 H ）-one衍生物。这种新颖的方法具有高收率，无金属且反应条件温和的优点。 图形概要
• A microwave-assisted copper-mediated tandem approach for fused quinazoline derivatives
  作者：Satyaveni Malasala、Anusha Polomoni、Sai Manohar Chelli、Swayamsidda Kar、Y. V. Madhavi、Srinivas Nanduri

  DOI：10.1039/d0ob02312d

  日期：——

  A method for the microwave-assisted copper-mediated oxidative coupling reaction of different aldehydes and quinazolines/benzimidazoles has been developed for the synthesis of fused-polycyclic systems via new C–N bond formation. The current methodology involves the use of environmentally benign NH4OAc as the amine source in the presence of 2-propanol as the solvent. This novel tandem reaction approach

  已开发出一种微波辅助铜介导的不同醛与喹唑啉/苯并咪唑的氧化偶联反应的方法，该方法可通过新的C–N键形成来合成稠合多环系统。当前的方法涉及在2-丙醇作为溶剂的存在下使用对环境无害的NH 4 OAc作为胺源。这种新颖的串联反应方法可以有效地快速而直接地获得复杂的稠合喹唑啉衍生物。
• Auto-Redox Reaction:  Tin(II) Chloride-Mediated One-Step Reductive Cyclization Leading to the Synthesis of Novel Biheterocyclic 5,6-Dihydro-quinazolino[4,3-<i>b</i>]quinazolin-8-ones with Three-Point Diversity
  作者：Abhijeet Deb Roy、Arunachalam Subramanian、Raja Roy

  DOI：10.1021/jo0518912

  日期：2006.1.1

  A tin(II) chloride-mediated short, efficient, and practical regioselective synthesis of biheterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity is reported. A one-step reductive transformation of 2-(2-nitrophenyl)-3H-quinazolin-4-one in various alcohols furnished the desired tetracyclic product in good yields with high purity.
• Luotonin A and Its Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents
  作者：Yanan Hao、Kaihua Wang、Ziwen Wang、Yuxiu Liu、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.0c04278

  日期：2020.8.19

  Plant diseases caused by viruses and fungi have posed a serious threat to global agricultural production. The discovery of new leads based on natural products is an important way to innovate pesticides. In this work, natural product luotonin A was found to have good antiviral activity against tobacco mosaic virus (TMV) for the first time. A series of luotonin A derivatives were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities systematically. Most compounds displayed better antiviral activities against TMV than commercial ribavirin. Compounds 9k, 12b, and 12d displayed about similar inhibitory effects as ningnanmycin (inhibitory rates of 55, 57, and 59% at 500 mu g/mL for inactivation, curative, and protection activities in vivo, respectively), the best antiviral agent at present, and emerged as novel antiviral leads for further research. We selected 9k for further antiviral mechanism research via transmission electron microscopy and molecular docking, which revealed that compound 9k can interact with TMV coat protein through the hydrogen bond, leading to its polymerization, thus preventing virus assembly. Further fungicidal activity tests showed that these compounds also showed broad-spectrum fungicidal activities against 14 kinds of phytopathogenic fungi. Especially, compound 14 with a 100% antifungal effect against Botrytis cinereal emerged as a lead for further research. This work provides a reference for the development of agricultural active ingredients based on Chinese medicine plants.
• Cu-Catalyzed Direct Diversification of 2-(2-Bromophenyl)quinazolin-4(3<i>H</i>)-ones through Orthogonal Reactivity Modulation
  作者：Satadru Chatterjee、Ravuri Srinath、Suvankar Bera、Krishnendu Khamaru、Afifa Rahman、Biswadip Banerji

  DOI：10.1021/acs.orglett.9b03428

  日期：2019.11.15

  A modular strategy to obtain three different products from a single substrate was developed. The present methodology unveils new step-economical and cost-efficient routes to access diverse fused quinazolinoquinazolinone derivatives which are not prevalent in literature. Owing to the importance of quinazolinones in therapeutics, quick access to the arena of these scaffolds could be a valuable addition to the scientific domain of heterocyclic chemistry.