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Issue 23, 2016
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Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

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Abstract

We have identified metal-free reaction conditions for the annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines to the corresponding acridine derivatives. The combination of trifluoroacetic acid (TFA), tert-butyl hydroperoxide (TBHP), dimethylsulfoxide (DMSO) and oxygen (O2) converted the cyclohexanone derivatives to an aromatic aryl product in moderate to good yields. The experimental results suggest that this process involves an aza-allyl oxidation intermediate.

Graphical abstract: Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

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Publication details

The article was received on 27 Aug 2016, accepted on 23 Oct 2016 and first published on 24 Oct 2016


Article type: Communication
DOI: 10.1039/C6GC02396G
Green Chem., 2016,18, 6241-6245

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    Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

    G. C. Senadi, G. K. Dhandabani, W. Hu and J. Wang, Green Chem., 2016, 18, 6241
    DOI: 10.1039/C6GC02396G

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