7,9-dimethyl-6H-indolo[2,3-b]quinoxaline

• 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: 7,9-dimethyl-6H-indolo[2,3-b]quinoxaline
• 英文别名: 7,9-Dimethyl-6H-indolo[2,3-b]chinoxalin；7,9-dimethyl-6H-indolo[2,3-b]quinoxaline；7,9-dimethyl-6H-indolo[3,2-b]quinoxaline
• 化学式: C₁₆H₁₃N₃
• mdl: MFCD03686009
• 分子量: 247.299
• InChiKey: JUOYIMZRGPYCIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,7-二甲基靛红 、 邻苯二胺 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 0.23h， 以92%的产率得到7,9-dimethyl-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  快速合成喹喔啉及其衍生物的环境友好属性

  摘要：

  摘要描述了一种使用羰基底物和苯二胺合成喹喔啉衍生物的简单、高效且环境友好的离子液体介导的方案。合成了一系列离子液体，通过 IR、1H 和 13C NMR 进行表征，并用作上述协议的溶剂和催化剂。评价了离子液体的催化活性，并讨论了催化活性与酸度之间的关系。还发现，在所有离子液体中，[Bmim]CF3SO3 是上述礼仪中最有效、最环保、最便宜的溶剂和催化剂。由于离子液体的环保性质和不使用单独的催化剂来推动反应的进行，该方法具有重要价值。

  DOI：

  10.1016/j.molstruc.2019.07.005

文献信息

• An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives
  作者：Sangeeta Bhargava、Pooja Soni、Deepti Rathore

  DOI：10.1016/j.molstruc.2019.07.005

  日期：2019.12

  Abstract A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship

  摘要描述了一种使用羰基底物和苯二胺合成喹喔啉衍生物的简单、高效且环境友好的离子液体介导的方案。合成了一系列离子液体，通过 IR、1H 和 13C NMR 进行表征，并用作上述协议的溶剂和催化剂。评价了离子液体的催化活性，并讨论了催化活性与酸度之间的关系。还发现，在所有离子液体中，[Bmim]CF3SO3 是上述礼仪中最有效、最环保、最便宜的溶剂和催化剂。由于离子液体的环保性质和不使用单独的催化剂来推动反应的进行，该方法具有重要价值。
• Buu-Hoi; Guettier, Bulletin de la Societe Chimique de France, 1946, p. 586,587
  作者：Buu-Hoi、Guettier

  DOI：——

  日期：——
• Sulfamic Acid: A Mild, Efficient, and Cost-Effective Catalyst for Synthesis of Indoloquinoxalines at Ambient Temperature
  作者：Pravin G. Hegade、Mansing M. Mane、Jayavant D. Patil、Dattaprasad M. Pore

  DOI：10.1080/00397911.2014.943345

  日期：2014.12.2

  A simple, cost-effective method for synthesis of indoloquinoxalines from isatin and o-phenylenediamine employing a catalytic amount of sulfamic acid at ambient temperature is reported. Moreover, the method is applicable for a variety of isatins, ninhydrin, 4-hydroxynaphthaquinone, and 1,2-diketones. The key features of the protocol include rapid reactions with good yields, simple workup procedure, and easy isolation of products.
• Cu doped CdS nanoparticles: A versatile and recoverable catalyst for chemoselective synthesis of indolo[2,3- b ]quinoxaline derivatives under microwave irradiation
  作者：Anshu Dandia、Vijay Parewa、Shuchi Maheshwari、Kuldeep S. Rathore

  DOI：10.1016/j.molcata.2014.07.022

  日期：2014.11

  CdS and Cu doped CdS NPs has been obtained successfully using safe agents through a simple aqueous chemical method and characterized by XRD, TEM, SEM, EDAX, UV/VIS and ICP-AES. These investigations revealed that the particle size of the synthesized materials were uniformly distributed in the range of 2-4 nm and confirm the Cu doping in the lattice of CdS NPs. These nanoparticles were exploited to study their catalytic activities toward the chemoselective synthesis of indolo[2,3-blquinoxalines by the reaction of isatins with 1,2-diamines in ethylene glycol under microwave irradiation. The method showed remarkable selectivity for indolo[2,3-b]quinoxalines over 3-imino-isatin, spirobenzimidazole, and ring-opened quinoxalinone derivatives. The catalytic activity of Cu doped CdS NPs was found to be about 18-fold higher under microwave irradiation (MW) as compared to the conventional method. Nanocatalyst plays a dual role of catalyst as well as susceptor, and enhances the overall capacity to absorb MW in the reaction mixture. Doping of Cu promotes the activity and selectivity of CdS nanoparticles indicated by high TOF value with good chemoselectivity. The surface acidity of NPs was measured by FTIR spectra of chemisorbed pyridine. Simple workup, mild reaction conditions, low cost, easy separation, and reusability of the catalyst are some advantages of this method. (C) 2014 Elsevier B.V. All rights reserved.
• Brönsted acid hydrotrope combined catalysis in water: a green approach for the synthesis of indoloquinoxalines and bis-tetronic acids
  作者：Arjun Kumbhar、Dhanaji Kanase、Suhas Mohite、Rajshri Salunkhe、Trushant Lohar

  DOI：10.1007/s11164-021-04430-w

  日期：2021.6

  The present work describes the applications of Brönsted acid hydrotrope combined catalyst (BAHC) as a mild, efficient and reusable catalyst for synthesis of indoloquinoxalines and bis-tetronic acids in water. Using BAHC, we synthesized many indoloquinoxaline derivatives from isatins and o-phenylene diamine using 10 mol% PTSA in 40% aqueous hydrotropic (NaPTS) solution at room temperature with 83–90%

  本工作描述了布朗斯台德酸水溶助长剂联合催化剂（BAHC）作为温和，有效和可重复使用的催化剂在水中合成吲哚并喹喔啉和双四反电子酸的应用。使用BAHC，我们在室温下，在40％的水溶水溶液（NaPTS）中使用10 mol％的PTSA，从靛红和邻苯二胺合成了许多吲哚喹喔啉衍生物，产率为83-90％。另一方面，在相同的BHAC中，四氢叶酸与醛/ Isatins的反应通过Knoevengel缩合-迈克尔加成途径形成双三叶四酸，产率为83-88％。此外，BAHC可以循环使用至第5个周期，而产品的收率却略有下降。极其简单的操作方法，绿色溶剂，