Issue 77, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
29 5 2018
Accepted
04 9 2018
First published
04 9 2018

Chem. Commun., 2018,54, 10866-10869

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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