辽宁石油化工大学学报 ›› 2023, Vol. 43 ›› Issue (6): 11-16.DOI: 10.12422/j.issn.1672-6952.2023.06.002

• 化学与化学工程 • 上一篇    下一篇

钌(Ⅱ)催化1⁃苯基⁃5⁃吡唑啉酮和碳酸亚乙烯酯的偶联反应

王华(), 王欣, 王贺, 周明东, 李蕾()   

  1. 辽宁石油化工大学 石油化工学院,辽宁 抚顺 113001
  • 收稿日期:2022-06-01 修回日期:2022-10-15 出版日期:2023-12-25 发布日期:2023-12-30
  • 通讯作者: 李蕾
  • 作者简介:王华(1996⁃),女,硕士研究生,从事有机合成方面的研究;E⁃mail:736871404@qq.com
  • 基金资助:
    国家自然科学基金项目(21702087);辽宁省教育厅项目(L2020033)

Ruthenium (Ⅱ)⁃Catalyzed Coupling Reaction of 1⁃Phenyl⁃2⁃Pyrazolin⁃5⁃One with Ethylene Carbonate

Hua WANG(), Xin WANG, He WANG, Mingdong ZHOU, Lei LI()   

  1. School of Petrochemical Engineering,Liaoning Petrochemical University,Fushun Liaoning 113001,China
  • Received:2022-06-01 Revised:2022-10-15 Published:2023-12-25 Online:2023-12-30
  • Contact: Lei LI

摘要:

设计了一个新颖的钌(Ⅱ)催化1?苯基?5?吡唑啉酮与碳酸亚乙烯基的C-C/C-N环化反应。 在该转化过程中,碳酸亚乙烯酯作为乙炔醇或乙炔的替代物,不需要额外添加任何氧化剂和碱。该反应具有广阔的底物范围和良好的官能团相容性,能够以42%~87%的收率得到一系列的1H?吡唑并[1,2?a]噌啉酮。提出了一种可能涉及到串联的C-H活化/分子内C-N形成/消除CO2或CO32-等历程的机制。此外,在执行克级反应时得到了一个令人满意的产率。

关键词: 钌(Ⅱ)催化, 1?苯基?5?吡唑啉酮, 碳酸亚乙烯酯, C-H活化, 1H?吡唑并[1,2?a]噌啉酮

Abstract:

A novel ruthenium(Ⅱ)?catalyzed C-H/C-N annulation of 1?phenyl?2?pyrazolin?5?one with ethylene carbonate was designed. In this transformation, the vinylene carbonate acts as an ethynol or alkyne surrogate without any external oxidant as well as bases involved. The reaction exhibits a broad substrate scope with excellent functional group compatibility, affording a series of 1H?pyrazolo[1,2?a]cinnolin?1?ones in 42%~87% yields. A possible mechanism involving a sequential C-H activation/intramolecular C-N bond formation/ CO2 or CO32- elimination is proposed. In addition, the reaction can also be carried out on a gram scale with satisfactory yield.

Key words: Ruthenium(Ⅱ) catalysis, 1?Phenyl?2?pyrazolin?5?one, Ethylene carbonate, C-H bond activation, 1H?Pyrazolo[1,2?a]cinnolin?1?one

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引用本文

王华, 王欣, 王贺, 周明东, 李蕾. 钌(Ⅱ)催化1⁃苯基⁃5⁃吡唑啉酮和碳酸亚乙烯酯的偶联反应[J]. 辽宁石油化工大学学报, 2023, 43(6): 11-16.

Hua WANG, Xin WANG, He WANG, Mingdong ZHOU, Lei LI. Ruthenium (Ⅱ)⁃Catalyzed Coupling Reaction of 1⁃Phenyl⁃2⁃Pyrazolin⁃5⁃One with Ethylene Carbonate[J]. Journal of Liaoning Petrochemical University, 2023, 43(6): 11-16.

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链接本文: https://journal.lnpu.edu.cn/CN/10.12422/j.issn.1672-6952.2023.06.002

               https://journal.lnpu.edu.cn/CN/Y2023/V43/I6/11