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Issue 23, 2018
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Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines

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Abstract

The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered.

Graphical abstract: Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines

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Publication details

The article was received on 08 Mar 2018, accepted on 22 May 2018 and first published on 22 May 2018


Article type: Paper
DOI: 10.1039/C8OB00588E
Citation: Org. Biomol. Chem., 2018,16, 4325-4332
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    Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines

    A. V. Aksenov, D. A. Aksenov, G. D. Griaznov, N. A. Aksenov, L. G. Voskressensky and M. Rubin, Org. Biomol. Chem., 2018, 16, 4325
    DOI: 10.1039/C8OB00588E

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