2-(5-phenyl-1,3,4-oxadiazol-2-yl)quinoxaline | 266345-03-3

• 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-(5-phenyl-1,3,4-oxadiazol-2-yl)quinoxaline
• 英文别名: 2-phenyl-5-(quinoxalin-2-yl)-1,3,4-oxadiazole
• CAS: 266345-03-3
• 化学式: C₁₆H₁₀N₄O
• 分子量: 274.282
• InChiKey: SSQZIBMVDLBEQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.7
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  benzoic acid (quinoxalin-2-yl)methylenehydrazide 在 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以94 %的产率得到2-(5-phenyl-1,3,4-oxadiazol-2-yl)quinoxaline
  参考文献：
  名称：

  Synthetic Access to Unsymmetric, Tridentate, Pyridyl-1,3,4-oxadiazole Complexants via Intramolecular Oxidative Annulation of Arylhydrazides with Heteroaryl Carbaldehydes

  摘要：

  DOI：

  10.1021/acs.joc.2c02421

文献信息

• Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides
  作者：Zhi-Hao Shang、Ji-Na Sun、Jiang-Shan Guo、Yuan-Yuan Sun、Wei-Zhao Weng、Zhen-Xiao Zhang、Zeng-Jing Li、Yan-Ping Zhu

  DOI：10.1016/j.tet.2019.130887

  日期：2020.2

  An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for

  据报道，甲基[azazeteroarenes]协议的氧化sp 3 C–H键可通过[4 +1]酰肼环合反应合成1,3,4-恶二唑。该方案通过在I 2 -DMSO存在下对甲基-氮杂杂环芳烃的sp 3 C–H键进行选择性氧化来实现1,3,4-恶二唑和喹啉连接的二杂环。该反应具有广泛的底物范围，并且对甲基-氮杂环杂芳烃和酰肼具有良好的官能团耐受性。
• Direct Heteroarylation of Tautomerizable Heterocycles into Unsymmetrical and Symmetrical Biheterocycles via Pd/Cu-Catalyzed Phosphonium Coupling
  作者：Abhishek Sharma、Dipak Vachhani、Erik Van der Eycken

  DOI：10.1021/ol300455e

  日期：2012.4.6

  The direct cross-coupling of tautomerizable heterocycles with various unfunctionalized heteroarenes has been achieved through PyBroP-mediated and Pd/Cu-catalyzed sequential C-OH/C-H activation. The methodology allows a facile entry into novel diazine-azole biheterocyclic frameworks. Moreover, an unprecedented Pd-catalyzed phosphonium homocoupling of tautomerizable heterocycles was also developed to afford a direct synthetic route to symmetrical 1,2-, 1,3-, and 1,4-bidiazine units.