2,3-diphenylquinoxaline-6-carbonitrile | 32388-07-1

• 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: 2,3-diphenylquinoxaline-6-carbonitrile
• 英文别名: 2,3-Diphenyl-6-quinoxalinecarbonitrile
• CAS: 32388-07-1
• 化学式: C₂₁H₁₃N₃
• 分子量: 307.354
• InChiKey: FCGFZVAKWAIWSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 盐酸 、 乙醇 、 tin(ll) chloride 作用下， 生成 2,3-diphenylquinoxaline-6-carbonitrile
  参考文献：
  名称：

  Borsche; Stackmann; Makaroff-Semljanski, Chemische Berichte, 1916, vol. 49, p. 2230

  摘要：

  DOI：

文献信息

• A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Victor V. Syakaev、Aidar T. Gubaidullin、Tat'yana N. Beschastnova、Dil'bar I. Adgamova、Aida I. Samigullina、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.10.045

  日期：2013.1

  A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange

  基于3-（苯并咪唑-2-基）喹喔啉-2（1 H）-与1,2-的环收缩，已开发出一种高效且通用的具有两个苯并咪唑片段的喹喔啉衍生物的合成方法。二氨基苯及其各种类型的取代和稠合衍生物。由于分子间和分子内过程，涉及桥联和相邻碳原子的大多数双-苯并咪唑基喹喔啉信号的几种形式之间的自缔合，质子交换，构象和/或互变异构交换，且NMR光谱中的苯并咪唑片段变宽。苯并咪唑片段与分子的喹喔啉核心之间的共轭作用比喹喔啉衍生物（10c）与其噻二唑[ f ]-（17）和吡咯并[ a ]-（19）环化了衍生物，导致整个分子的平面度更大。
• The Direct Synthesis of Imines, Benzimidazoles and Quinoxalines from Nitroarenes and Carbonyl Compounds by Selective Nitroarene Hydrogenation Employing a Reusable Iron Catalyst
  作者：Christoph Bäumler、Rhett Kempe

  DOI：10.1002/chem.201801525

  日期：2018.6.26

  robust and reusable iron catalyst, which permits the selective hydrogenation of nitroarenes in the presence of hydrogenation‐sensitive functional groups. Based on the selectivity pattern observed, the direct iron‐catalyzed synthesis of imines and benzimidazoles from nitroarenes and aldehydes becomes feasible. In addition, we introduce the direct synthesis of quinoxalines from nitroarenes and diketones

  富含稀土的金属对“贵金属”的“取代”是催化的理想目标，也是保存稀有元素的一种可能方法。如果观察到新的选择性图谱允许发展新的偶联反应，则“取代”特别有吸引力。在本文中，我们报道了一种新颖，坚固且可重复使用的铁催化剂，该催化剂可在对氢化敏感的官能团存在的情况下对硝基芳烃进行选择性加氢。根据观察到的选择性模式，从硝基芳烃和醛直接铁催化合成亚胺和苯并咪唑变得可行。此外，我们介绍了使用我们的催化剂从硝基芳烃和二酮直接合成喹喔啉的方法。
• In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
  作者：Kashyap J. Tamuli、Shyamalendu Nath、Manobjyoti Bordoloi

  DOI：10.1002/jhet.4231

  日期：2021.4

  Substituted quinoxaline derivatives are traditionally synthesized by co‐condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o‐phenylenediamine and 1,2‐diketones using cheap and biodegradable itaconic acid as a mild acid

  取代的喹喔啉衍生物传统上是通过各种起始原料的共缩合反应合成的。在本文中，我们描述了一种新型的环境友好的水合成路线，用于合成结构和电子形式多样的90喹喔啉类化合物，并容易获得取代的邻氨基苯甲酸。苯二胺和1,2-二酮在1小时内使用廉价且可生物降解的衣康酸作为温和的酸性促进剂。该反应在室温下进行，该过程通过环缩合反应进行，然后获得上述含氮杂环加合物，而无需进行柱色谱分离，总收率不超过96％。催化剂的简单性，高效率和可重复使用性将该反应条件称为“绿色合成”，这使其可用于克级至克级的合成转化中。
• General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines
  作者：Zhijian Zhao、David D Wisnoski、Scott E Wolkenberg、William H Leister、Yi Wang、Craig W Lindsley

  DOI：10.1016/j.tetlet.2004.04.144

  日期：2004.6

  Functionalized quinoxalines and heterocyclic pyrazines are expediently prepared in excellent yields (69–99%) from common 1,2-diketone intermediates under microwave irradiation. In addition to being general for a variety of aryl/heteroaryl 1,2-diamines and 1,2-diketones, this protocol suppresses the formation of polymeric species, characteristic of traditional thermal conditions.

  方便地在微波辐射下，从常见的1,2-二酮中间体以优异的收率（69–99％）制备功能化的喹喔啉和杂环吡嗪。除了可以广泛用于各种芳基/杂芳基1,2-二胺和1,2-二酮外，该方案还可以抑制传统热条件下的聚合物种类的形成。
• Surfactant micelles as microreactors for the synthesis of quinoxalines in water: scope and limitations of surfactant catalysis
  作者：Dinesh Kumar、Kapileswar Seth、Damodara N. Kommi、Srikant Bhagat、Asit K. Chakraborti

  DOI：10.1039/c3ra41038b

  日期：——

  The scope and limitations of surfactants as catalysts for the synthesis of quinoxalines using microreactors made of the surfactants in water has been assessed. The catalytic potential followed the order: non-ionic surfactants > anionic surfactants > Brønsted acid surfactants > cationic surfactants. The non-ionic surfactant, Tween 40, is the most effective catalyst affording excellent yields within a short reaction time at room temperature and is compatible with different variations of the 1,2-diketones and 1,2-diamines. The reaction medium (spent water) containing the catalyst, as well as the catalyst itself (recovered Tween 40) can be reused for five consecutive reactions. The better catalytic efficiency of the surfactant (Tween 40) compared to the various Lewis/Brønsted acids, as well as the surfactant combined Lewis acid, suggests that surfactants, which generate microreactor assemblies at the interface, are better suited as catalytic aids to promote organic reactions in water. The inferior results obtained in organic solvents, which provide a homogeneous reaction mixture compared to those obtained in water, indicate the specific role of water. This has been depicted as a synergistic dual activation through the hydrogen bond mediated formation of supramolecular assemblies involving a water dimer and the reactants. The catalytic assistance of the surfactant could be ascribed to the ability of the surfactant molecule to undergo hydrophobic and hydrogen bond forming interactions with water and the reactants in orienting the reactants at the water interface and encapsulating inside the microreactors to facilitate the cyclocondensation.

  已经评估了表面活性剂作为催化剂在水相中使用微反应器合成喹噁啉的范围和局限性。催化潜力的顺序为：非离子表面活性剂 > 阴离子表面活性剂 > 布朗斯特酸表面活性剂 > 阳离子表面活性剂。非离子表面活性剂Tween 40是最有效的催化剂，在室温下能够在短时间内提供优异的产率，并且对不同类型的1,2-二酮和1,2-二胺具有良好的兼容性。含有催化剂的反应介质（使用过的水）以及催化剂本身（回收的Tween 40）可以重复使用五次连续反应。与各种路易斯/布朗斯特酸及其复合路易斯酸相比，表面活性剂（Tween 40）展现出更好的催化效率，表明产生微反应器组装的表面活性剂更适合作为促进水中有机反应的催化辅助剂。在有机溶剂中获得的结果较差，这意味着有机溶剂提供一致的反应混合物，而在水中获得的结果表明水的特定作用。这一过程被描述为通过氢键介导的超分子组装的协同双重活化，涉及氢水二聚体和反应物。表面活性剂的催化辅助作用可以归因于表面活性剂分子与水和反应物之间进行疏水和氢键形成相互作用的能力，这有助于在水界面上定向反应物并将其封装在微反应器内，从而促进环缩合反应。