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Issue 18, 2017
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Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

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Abstract

The indole nucleus is a privileged heterocyclic scaffold, which is present in several natural and synthetic compounds. New synthetic strategies to access functionalized indoles have therefore attracted the attention of both synthetic and medicinal chemists over the decades. In this study, the bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles and 1,3-di(1H-indol-3-yl)benzene derivatives is reported for the first time. Using 3-methylindole with cyclopentanone, cyclohexanone, and cycloheptanone results in new and different synthetic pathways. The plausible reaction mechanisms are presented and supported with DFT (M06-2X/6-31+G(d,p)) calculations.

Graphical abstract: Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

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Publication details

The article was received on 05 Jun 2017, accepted on 27 Jul 2017 and first published on 27 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01987D
Citation: New J. Chem., 2017,41, 9674-9687
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    Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

    H. Kilic, S. Bayindir, E. Erdogan, S. Agopcan Cinar, F. A. S. Konuklar, S. K. Bali, N. Saracoglu and V. Aviyente, New J. Chem., 2017, 41, 9674
    DOI: 10.1039/C7NJ01987D

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