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Issue 77, 2018
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Gold-catalyzed annulations of N-aryl ynamides with benzisoxazoles to construct 6H-indolo[2,3-b]quinoline cores

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Abstract

This work reports new annulations of N-aryl ynamides with benzisoxazoles to form 6H-indolo[2,3-b]quinoline derivatives. The synthetic utility of this new method is manifested by its applicability to access naturally occurring alkaloids including norcryptotackeine, neocryptolepine and 11-methylneocryptol-epine. Our experimental data indicate that high-temperature conditions allow N-aryl nucleophiles to become conformationally flexible, rendering the attack at gold carbenes effective to generate reactive indoles that attack again the benzaldehyde to furnish the observed products.

Graphical abstract: Gold-catalyzed annulations of N-aryl ynamides with benzisoxazoles to construct 6H-indolo[2,3-b]quinoline cores

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Publication details

The article was received on 29 May 2018, accepted on 04 Sep 2018 and first published on 04 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC04264K
Citation: Chem. Commun., 2018,54, 10866-10869
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    Gold-catalyzed annulations of N-aryl ynamides with benzisoxazoles to construct 6H-indolo[2,3-b]quinoline cores

    M. Tsai, C. Wang, A. S. Kulandai Raj and R. Liu, Chem. Commun., 2018, 54, 10866
    DOI: 10.1039/C8CC04264K

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