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Issue 39, 2017
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AgOTf-catalyzed sequential synthesis of 4-isoquinolones via oxidative ring opening of aziridines and aza-Michael addition

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Abstract

An efficient AgOTf-catalyzed sequential reaction involving the oxidative ring-opening of aziridines by DMSO and aza-Michael addition has been developed. A series of 2,3-dihydro-4(1H)-isoquinolones were afforded in moderate to good yields by the formation of one new C[double bond, length as m-dash]O bond and one new C–N bond. The features of this sequential reaction include high bonding efficiency, use of a catalytic amount of catalysts, a broad substrate scope and mild conditions. This methodology provides a good choice for constructing the libraries of 2,3-dihydro-4(1H)-isoquinolones.

Graphical abstract: AgOTf-catalyzed sequential synthesis of 4-isoquinolones via oxidative ring opening of aziridines and aza-Michael addition

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Publication details

The article was received on 30 Aug 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02167D
Citation: Org. Biomol. Chem., 2017,15, 8308-8312
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    AgOTf-catalyzed sequential synthesis of 4-isoquinolones via oxidative ring opening of aziridines and aza-Michael addition

    S. Xing, H. Cui, N. Gu, Y. Li, K. Wang, D. Tian, J. Qin and Q. Liu, Org. Biomol. Chem., 2017, 15, 8308
    DOI: 10.1039/C7OB02167D

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