12-bromo-dibenzo[f,h]pyrido[2,3-b]quinoxaline

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 12-bromo-dibenzo[f,h]pyrido[2,3-b]quinoxaline
• 英文别名: 12-Brom-dibenzo[f,h]pyrido[2,3-b]chinoxalin；12-Bromodibenzo[f,H]pyrido[2,3-b]quinoxaline；19-bromo-15,17,22-triazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2,4,6,8,10,12,14,16(21),17,19-undecaene
• 化学式: C₁₉H₁₀BrN₃
• 分子量: 360.212
• InChiKey: GZWSPBBCDBZHOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲苯硼酸 、 12-bromo-dibenzo[f,h]pyrido[2,3-b]quinoxaline 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以66%的产率得到19-(4-Methylphenyl)-15,17,22-triazapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(22),2,4,6,8,10,12,14,16(21),17,19-undecaene
  参考文献：
  名称：

  Synthesis of quinoxalines and pyrido[2,3-b]pyrazines by Suzuki–Miyaura cross-coupling reaction

  摘要：

  以芳香1,2-二胺和1,2-二酮化合物的缩合反应合成了溴取代的喹喏啉和吡啶[2,3-b]呲唑。这些化合物被用作后续缩合修饰的常见中间体，通过铃木-宫浦偶联反应形成芳基取代的喹喏啉和吡啶[2,3-b]呲唑。通过在四氢呋喃（THF）中使用K2CO3作为碱，加入Pd(dppf)Cl2·CH2Cl2并在回流温度下进行偶联反应，成功实现了芳基取代的喹喏啉和吡啶[2,3-b]呲唑衍生物的高效合成，且产率有所提高。

  DOI：

  10.1007/s11164-015-2377-7
• 作为产物：
  描述：

  在 trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane 、 溴化铵 作用下， 以 水 为溶剂， 以80 %的产率得到12-bromo-dibenzo[f,h]pyrido[2,3-b]quinoxaline
  参考文献：
  名称：

  温和条件下反式-3,5-二氢过氧-3,5-二甲基-1,2-二氧戊环促进非反应性芳香族底物在水中的氧化溴化

  摘要：

  发表于《国际有机制备和程序：有机合成新期刊》（第 56 卷，第 1 期，2024 年）

  DOI：

  10.1080/00304948.2023.2219199

文献信息

• Synthesis of quinoxaline, benzimidazole and pyrazole derivatives under the catalytic influence of biosurfactant-stabilized iron nanoparticles in water
  作者：Satyanarayan M. Arde、Audumbar D. Patil、Ananda H. Mane、Prabha R. Salokhe、Rajashri S. Salunkhe

  DOI：10.1007/s11164-020-04240-6

  日期：2020.11

  thermogravimetric analysis, and BET analysis. The FeNPs were amorphous in nature with average particle size ~ 19 nm and successfully employed as heterogeneous catalyst for the synthesis of quinoxaline, benzimidazole, and pyrazole derivatives in aqueous medium at ambient conditions. The FeNPs could be recycled up to five times with modest change in the catalytic activity. Graphic abstract

  摘要 我们已经报告了可再生天然资源乳香锯缘青蟹植物的叶片提取物的无定形铁纳米颗粒（FeNPs）的合成，表征和催化应用。通过添加金合欢荚果荚提取物原位稳定合成的FeNPs作为生物表面活性剂（pH 3.11）。使用紫外可见光谱，X射线衍射分析，选定区域电子衍射，能量色散X射线光谱，扫描电子显微镜，透射电子显微镜，X射线光电子光谱，热重分析，和BET分析。FeNPs本质上是无定形的，平均粒径约为19 nm，已成功地用作在环境条件下在水性介质中合成喹喔啉，苯并咪唑和吡唑衍生物的非均相催化剂。FeNPs可以循环使用多达五次，而催化活性变化不大。 图形摘要
• Brönsted acid hydrotrope combined catalyst for environmentally benign synthesis of quinoxalines and pyrido[2,3-b]pyrazines in aqueous medium
  作者：Arjun Kumbhar、Santosh Kamble、Madhuri Barge、Gajanan Rashinkar、Rajashri Salunkhe

  DOI：10.1016/j.tetlet.2012.03.097

  日期：2012.5

  A new Brönsted acid hydrotrope combined catalyst (BAHC) has been developed and applied in acid catalyzed synthesis of pyrido[2,3-b]pyrazines and quinoxalines in an aqueous medium at ambient temperature with excellent yields. Interestingly, the catalyst can be easily recovered after the reactions and reused. Furthermore, BAHC catalyst worked well and avoids the use of organic solvents. We have reported

  已开发出一种新的布朗斯台德酸水溶助长剂联合催化剂（BAHC），并用于在室温下在水性介质中以优异的收率对吡啶并[2,3- b ]吡嗪和喹喔啉进行酸催化合成。有趣的是，催化剂可以在反应后容易地回收并再利用。此外，BAHC催化剂效果很好，并且避免使用有机溶剂。我们已经在本文中报道了在大气和人类生存中具有较少灾难性影响的合成途径。
• Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
  作者：Maasoumeh Jafarpour、Abdolreza Rezaeifard、Mahboube Ghahramaninezhad、Tooba Tabibi

  DOI：10.1039/c3nj00058c

  日期：——

  Crystalline nanobelts of α-MoO3 have been obtained successfully using novel and safe agents through a simple and safe sol–gel method (polymerizing–complexing) and characterized by XRD, FT-IR, Raman spectroscopies, high resolution transmission electron microscopy (HRTEM), scanning electron microscopy (SEM) and the temperature programmed desorption (TPD) of ammonia. An orthorhombic lattice system for nano-MoO3 was established. The HRTEM images showed that the nanobelt morphology of α-MoO3 mostly ranged from 20–70 nm in width and 200–400 nm in length. The ammonia TPD profile demonstrated strong acidic sites. The spectral and analysis data confirmed the effectiveness of the method for the preparation of α-MoO3 nanobelts by prevention of grain growth or agglomeration of the particles. The nanostructured MoO3 exhibited a high efficiency in catalyzing the condensation reaction of various 1,2-diamine and carbonyl compounds for synthesis of heterocyclic compounds. The recovery of the title heterogenous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk material.

  成功利用新颖且安全的试剂，通过简单安全的溶胶-凝胶法（聚合-络合）获取了α-MoO3的晶态纳米带，并通过XRD、FT-IR、拉曼光谱、高分辨率透射电子显微镜（HRTEM）、扫描电子显微镜（SEM）及氨的程序升温脱附（TPD）进行了表征。建立了纳米-MoO3的正交晶格体系。HRTEM图像显示α-MoO3的纳米带形态宽度多在20-70纳米之间，长度为200-400纳米。氨TPD谱图表明存在强酸性位点。光谱和分析数据确认了该方法在防止颗粒的晶粒生长或聚集方面对于制备α-MoO3纳米带的有效性。纳米结构的MoO3在催化多种1,2-二胺和羰基化合物缩合反应合成杂环化合物方面表现出高效能。该异质纳米催化剂的回收简单高效，其催化活性与块体材料显著不同。
• A novel protocol for selective synthesis of monoclinic zirconia nanoparticles as a heterogeneous catalyst for condensation of 1,2-diamines with 1,2-dicarbonyl compounds
  作者：Maasoumeh Jafarpour、Elham Rezapour、Mahboobe Ghahramaninezhad、Abdolreza Rezaeifard

  DOI：10.1039/c3nj00655g

  日期：——

  ZrO2 nanocatalyst has been obtained successfully using novel and safe agents through a simple and safe sol–gel method (polymerizing–complexing) and characterized by XRD, FT-IR, Raman spectroscopies and transmission electron microscopy (TEM). Raman spectroscopies and XRD results indicated only formation of monoclinic zirconia. TEM images revealed spherical nanoparticles with 20–40 nm diameter range. The spectral and analysis data confirmed the effectiveness of the method for preparation of monoclinic zirconia by preventing grain growth or agglomeration of particles. The nanostructured ZrO2 exhibited high efficiency in catalyzing condensation of various 1,2-diamine and 1,2-dicarbonyl compounds for the synthesis of heterocyclic compounds. The recovery of the title heterogeneous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk one.

  ZrO2纳米催化剂通过一种简单安全的溶胶-凝胶法（聚合-络合）成功获得，使用了新颖和安全的试剂，并通过XRD、FT-IR、拉曼光谱和透射电子显微镜（TEM）进行了表征。拉曼光谱和XRD结果表明仅形成了单斜相锆石。TEM图像显示出直径范围为20-40纳米的球形纳米颗粒。光谱和分析数据证实了该方法在制备单斜相锆石方面的有效性，防止了颗粒的晶粒生长或团聚。纳米结构的ZrO2在催化各种1,2-二胺和1,2-二酮化合物的缩合反应以合成杂环化合物方面表现出高效能。所述异相纳米催化剂的回收工作简单高效，其催化活性与批量催化剂显著不同。
• A zirconium Schiff base complex immobilized on starch-coated maghemite nanoparticles catalyzes heterogeneous condensation of 1,2-diamines with 1,2-dicarbonyl compounds
  作者：Maasoumeh Jafarpour、Abdolreza Rezaeifard

  DOI：10.1007/s11243-015-0012-5

  日期：2016.3

  A magnetically separable zirconium Schiff base nanocatalyst was synthesized under ultrasonic agitation. TEM images revealed a uniform spherical particle shape with average size of 10–14 nm for the as-prepared catalyst. The catalytic performance of ZrOL2@SMNP in the heterogeneous condensation of various 1,2-diamines and 1,2-dicarbonyls for the synthesis of heterocyclic compounds in ethanol has been explored.

  一种磁性可分离的锆Schiff碱纳米催化剂在超声搅拌下合成。透射电子显微镜（TEM）图像显示，所制备催化剂呈现均匀的球形颗粒，平均尺寸为10–14纳米。研究了ZrOL2@SMNP在不同1,2-二胺和1,2-二羰基化合物在乙醇中合成杂环化合物的异相缩合反应中的催化性能。