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Issue 27, 2018
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Synthetic access to isoxazoline-functionalized isoquinolines via microwave-assisted iminoxyl radical-participated cascade cyclization of vinyl isocyanides

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Abstract

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 β,γ-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.

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

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Supplementary files

Article information


Submitted
25 May 2018
Accepted
15 Jun 2018
First published
18 Jun 2018

Org. Biomol. Chem., 2018,16, 4996-5005
Article type
Paper

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

Y. Xu, H. Chen, W. Li, Q. Xie, L. Yu and L. Shao, Org. Biomol. Chem., 2018, 16, 4996
DOI: 10.1039/C8OB01229F

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