N-benzyl-3-phenylquinoxaline-2-carboxamide | 1609929-64-7

• 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: N-benzyl-3-phenylquinoxaline-2-carboxamide
• CAS: 1609929-64-7
• 化学式: C₂₂H₁₇N₃O
• 分子量: 339.396
• InChiKey: IGJDLHXNPHUERX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl (2-((1-(benzylamino)-1,3-dioxo-3-phenylpropan-2-yl)amino)phenyl)carbamate 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以40%的产率得到N-benzyl-3-phenylquinoxaline-2-carboxamide
  参考文献：
  名称：

  A Robust Protocol for the Synthesis of Quinoxalines and 5H-Benzo[e][1,4]di­azepines via the Acidless Ugi Reaction

  摘要：

  Concise two-step, one-pot protocols for the syntheses of quinoxalines and 5H-benzo[e][1,4]diazepines are reported. An acidless' Ugi reaction followed by a Boc-deprotection-cyclization sequence is shown to produce arrays of both functionalized scaffolds in good yield. Mono-N-Boc-protected diamines are employed to access quinoxalines and an analogous benzylic amine affords access to 5H-benzo[e][1,4]diazepines in conjunction with supporting reagents in the acidless' Ugi reaction. Both methodologies are robust, straightforward, and allow installation of at least three points of diversity in the resulting scaffolds.

  DOI：

  10.1055/s-0033-1339135

文献信息

• A facile method for building fused quinoxaline-quinolinones via an acidless post-Ugi cascade reaction
  作者：Yong Li、Jie Lei、Jia Xu、Dian-Yong Tang、Zhong-Zhu Chen、Jin Zhu、Chuan Xu

  DOI：10.1016/j.cclet.2016.10.027

  日期：2017.3

  A series of quinolino[3,4-b] quinoxalin-6(5H)-ones have been synthesized using an Ugi/deprotection/cyclization (UDC) strategy, followed by a nucleophilic aromatic substitution reaction. This facile microwave-assisted method provided good yields and could potentially be used for the construction of a diverse library of quinolino[3,4-b] quinoxalin-6(5H)-ones for high-throughput screening in medicinal chemistry. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Ugi-Based Approaches to Quinoxaline Libraries
  作者：Jhonny Azuaje、Abdelaziz El Maatougui、Xerardo García-Mera、Eddy Sotelo

  DOI：10.1021/co500036n

  日期：2014.8.11

  An expedient and concise Ugi-based unified approach for the rapid assembly of quinoxaline frameworks has been developed. This convergent and versatile method uses readily available commercial reagents, does not require advanced intermediates, and exhibits excellent bond-forming efficiency, thus exemplifying the operationally simple synthesis of quinoxaline libraries.