4-ethylpyrrolo[1,2-a]quinoxaline | 1398949-40-0

• 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: 4-ethylpyrrolo[1,2-a]quinoxaline
• 英文别名: 4-ethylpyrrolo[1,2-α]quinoxaline
• CAS: 1398949-40-0
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: WXMSRWLJBZBXIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-(1-phenyl-1H-pyrrol-2-yl)propan-1-one O-acetyl oxime 在 iron(III)-acetylacetonate 作用下， 以 溶剂黄146 为溶剂， 反应 0.25h， 以56%的产率得到4-ethylpyrrolo[1,2-a]quinoxaline
  参考文献：
  名称：

  Iron-Catalyzed Intramolecular C(sp²)–N Cyclization of 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward Pyrrolo[1,2-a]quinoxaline Derivatives

  摘要：

  An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N-O bond cleavage and intramolecular directed C-H arylation reactions in acetic acid.

  DOI：

  10.1021/acs.joc.5b00915

文献信息

• Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2-a]quinoxalines from 2-(1H-Pyrrol-1-yl)anilines and Alkylboronic Acids
  作者：Rulong Yan、Xin Guan

  DOI：10.1055/s-0037-1610743

  日期：2020.3

  A radical pathway for the construction of pyrrolo[1,2-a]quinoxalines by using 2-(1H-pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operations. Alkylboronic acids are used for the construction of pyrrolo[1,2-a]quinoxaline derivatives, and the desired products are obtained in moderate yields

  已经开发了使用 2-(1H-pyrrol-1-yl) 苯胺和烷基硼酸构建吡咯并 [1,2-a] 喹喔啉的自由基途径。该工艺的特点包括铜催化、易获得的起始材料和简单的操作。烷基硼酸用于构建吡咯并[1,2-a]喹喔啉衍生物，以中等收率获得所需产物。
• Efficient synthesis of pyrrolo[1,2-a]quinoxalines catalyzed by a Brønsted acid through cleavage of C–C bonds
  作者：Caixia Xie、Lei Feng、Wanli Li、Xiaojun Ma、Xinkun Ma、Yihan Liu、Chen Ma

  DOI：10.1039/c6ob01401a

  日期：——

  An efficient and convenient one-pot domino reaction for the direct synthesis of pyrrolo[1,2-a]quinoxalines has been developed. This approach utilizes an imine formation reaction, SEAr reaction and cleavage of C–C bonds catalyzed by a Brønsted acid. β-Diketones and β-keto esters are both well tolerated to give the corresponding products in moderate to excellent yields.

  已经开发了用于直接合成吡咯并[1,2- a ]喹喔啉的有效且方便的一锅多米诺反应。该方法利用用于形成亚胺的反应，S È氩反应和裂解由布朗斯台德酸催化的C-C键。β-二酮和β-酮​​酯均具有良好的耐受性，可以以中等至极好的收率得到相应的产物。
• Mo–Catalyzed One‐Pot Synthesis of <i>N</i> ‐Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent‐Tuned Photophysical Properties
  作者：Raquel Hernández‐Ruiz、Rubén Rubio‐Presa、Samuel Suárez‐Pantiga、María R. Pedrosa、Manuel A. Fernández‐Rodríguez、M. José Tapia、Roberto Sanz

  DOI：10.1002/chem.202102000

  日期：2021.9.24

  reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a

  据报道，催化多米诺还原-亚胺形成-分子内环化-氧化用于一般合成各种生物学相关的N-多杂环，例如喹喔啉和喹啉稠合衍生物以及菲啶。一种简单、易得且环保的二氧代钼(VI)络合物已被证明是一种高效且多功能的催化剂，可用于转化涉及多种氧化还原过程的各种起始硝基芳烃。这不仅是一种可持续、步骤经济且耐空气和耐湿的方法，而且值得强调的是，序列第一步中产生的废物副产物被回收并合并到最终的目标分子中，从而改善了整体合成效率。此外，选定的吲哚喹喔啉在环己烷和甲苯中进行了光物理表征，烷基衍生物的荧光量子产率高于 0.7。
• An environmentally friendly approach to pyrrolo[1,2-a]quinoxalines using oxygen as the oxidant
  作者：Chao Wang、Yun Li、Jianfei Zhao、Bin Cheng、Huifei Wang、Hongbin Zhai

  DOI：10.1016/j.tetlet.2016.07.041

  日期：2016.8

  We have developed an environmentally benign and practical protocol for the synthesis of pyrrolo[1,2-a]quinoxalines, which represent ubiquitous structural units common to a number of biologically active compounds. This synthetic system features simple operation and using clean oxidant, as well as mild reaction conditions. Both aromatic and aliphatic aldehydes can be used for the reaction and the products

  我们已经开发了一种环境友好且实用的合成吡咯并[1,2- a ]喹喔啉的方法，吡咯并[1,2- a ]喹喔啉代表了许多生物活性化合物共有的普遍存在的结构单元。该合成系统操作简单，使用清洁的氧化剂，反应条件温和。芳族和脂族醛均可用于该反应，并且以良好至优异的产率获得产物。
• One-Pot Synthesis of Pyrrolo[1,2-<i>a</i>]quinoxaline Derivatives via Iron-Promoted Aryl Nitro Reduction and Aerobic Oxidation of Alcohols
  作者：Maria de Fatima Pereira、Valérie Thiéry

  DOI：10.1021/ol302006b

  日期：2012.9.21

  describe a new one-pot method to synthesize 4,7-substituted pyrrolo[1,2-a]quinoxalines and related heterocyles through a cascade of redox reactions/imine formation/intramolecular cyclization. This procedure tolerates readily available substituted 1-(2-nitrophenyl)pyrrole derivatives and aliphatic or benzylic alcohols as starting materials using iron powder and acidic conditions. This is the first example

  在这里，我们描述了一种新的一锅法，通过级联的氧化还原反应/亚胺形成/分子内环化反应来合成4,7-取代的吡咯并[1,2- a ]喹喔啉和相关杂环。该方法耐受使用铁粉和酸性条件容易获得的取代的1-（2-硝基苯基）吡咯衍生物和脂族或苄基醇作为起始原料。这是在一个罐中通过铁介导的芳基硝基还原和酒精的好氧氧化构造N-杂环的第一个例子。