4.6 Article

Synthetic access to isoxazoline-functionalized isoquinolines via microwave-assisted iminoxyl radical-participated cascade cyclization of vinyl isocyanides

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 16, 期 27, 页码 4996-5005

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01229f

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资金

  1. National Natural Science Foundation of China [81473076, 81673292, 81502985]
  2. National Basic Research Program of China (973 Program) [2015CB931804]
  3. Science and Technology Commission of Shanghai Municipality [15431900100]

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A convenient microwave-assisted method for the synthesis of isoxazoline-functionalized isoquinolines via the n-Bu4NI (TBAI) catalyzed radical cascade cyclization of vinyl isocyanides with beta,gamma-unsaturated ketoximes has been described. The methodology presented here achieves a wide substrate scope and good to excellent yields. A radical mechanism is proposed, which is supported by the intermolecular competing kinetic isotope effect (KIE) experiment and the radical trapping experiment.

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