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Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones

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Abstract

A highly regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates to afford N-1 and C-2 indolyl diketones in moderate to good yields is described. Notably, the control of regioselectivity is achieved by small changes in the Cu catalyst, additive and solvent. Importantly, the intermediates for N-1 and C-2 diacylation were detected and two plausible pathways were also proposed.

Graphical abstract: Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones

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Publication details

The article was received on 24 Jul 2018, accepted on 11 Sep 2018 and first published on 11 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01776J
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones

    D. Pan, J. Chu, X. Gao, C. Wang, Q. Meng, H. Chi, Y. Dong, C. Duan and Z. Zhang, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01776J

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