4.8 Article

Ruthenium(II)-Catalyzed C-C/C-N Coupling of 2-Arylquinazolinones with Vinylene Carbonate: Access to Fused Quinazolinones

Journal

ORGANIC LETTERS
Volume 23, Issue 3, Pages 995-999

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04200

Keywords

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Funding

  1. National Natural Science Foundation of China [21702087, 21801105]
  2. LiaoNing Revitalization Talents Program [XLYC1907010, XLYC1902085]
  3. Research Project Fund of Liaoning Provincial Department of Education [L2020033]
  4. Talent Scientific Research Fund of Liaoning Shihua University [2016XJJ-078, 2016XJJ-079]

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This work presents a ruthenium(II)-catalyzed C-C/C-N annulation of 2-arylquinazolinones with vinylene carbonate to synthesize fused quinazolinones, showing excellent substrate tolerance and functional-group compatibility. The use of vinylene carbonate as an ethynol surrogate without external oxidants is highlighted, along with preliminary mechanistic studies and a proposed catalytic cycle.
In this work, ruthenium(II)-catalyzed C-C/C-N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.

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