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Switchable intramolecular oxidative amidation of 4-arylquinoline-3-carboxamides: divergent access to dibenzo[c,f][2,7]naphthyridinones and spirocyclohexadienones

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Abstract

A Na2S2O8-mediated switchable oxidative cyclization of 4-arylquinoline-3-carboxamides is described. The catalyst-free reaction affords dibenzo[c,f][2,7]naphthyridinones in 32–78% yields in refluxing EtOAc/H2O or CH3CN/H2O, while the AgNO3-catalyzed reaction delivers spirocyclohexadienones in 25–72% yields in CH3COCH3/H2O at room temperature.

Graphical abstract: Switchable intramolecular oxidative amidation of 4-arylquinoline-3-carboxamides: divergent access to dibenzo[c,f][2,7]naphthyridinones and spirocyclohexadienones

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Publication details

The article was received on 14 Aug 2017, accepted on 19 Oct 2017 and first published on 20 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00720E
Citation: Org. Chem. Front., 2017, Advance Article
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    Switchable intramolecular oxidative amidation of 4-arylquinoline-3-carboxamides: divergent access to dibenzo[c,f][2,7]naphthyridinones and spirocyclohexadienones

    Q. Wang, L. Luo, J. Wang, X. Peng, C. Hu and H. Wang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00720E

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