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Issue 47, 2018
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Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones

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Abstract

A cyclization cascade initiated by the addition of a silyl radical to an electron-deficient carbon–carbon double bond of N-arylacrylamides, followed by intramolecular cyano group insertion and homolytic aromatic substitution has been reported. In the presence of di-lauroyl peroxide (LPO), under metal-free conditions, several readily available hydrosilanes were successfully used as the source of silyl radicals and a series of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones were obtained in moderate to good yields.

Graphical abstract: Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones

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Publication details

The article was received on 29 Oct 2018, accepted on 19 Nov 2018 and first published on 21 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02670J
Citation: Org. Biomol. Chem., 2018,16, 9223-9229
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    Silyl radical initiated radical cascade addition/cyclization: synthesis of silyl functionalized 4H-pyrido[4,3,2-gh]phenanthridin-5(6H)-ones

    C. Zhang, J. Pi, L. Wang, P. Liu and P. Sun, Org. Biomol. Chem., 2018, 16, 9223
    DOI: 10.1039/C8OB02670J

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