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Selective access to dipyrazolo-fused pyridines via formal [3 + 2 + 1] heteroannulation of methyl ketones with pyrazol-5-amines

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Abstract

A fascinating new form of the Hantzsch reaction with methyl ketones and pyrazol-5-amines for the selective synthesis of dipyrazolo-fused pyridines has been discovered. This special [3 + 2 + 1] heteroannulation was accomplished via the domino generation of two C–C bonds and one C–N bond. Preliminary mechanistic studies indicated that the I2/DMSO system realized the oxidative carbonylation of Csp3–H of methyl ketones, while Cu(OTf)2 acted as a relay reagent to accelerate this transformation.

Graphical abstract: Selective access to dipyrazolo-fused pyridines via formal [3 + 2 + 1] heteroannulation of methyl ketones with pyrazol-5-amines

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Publication details

The article was received on 16 Oct 2017, accepted on 13 Nov 2017 and first published on 14 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00941K
Citation: Org. Chem. Front., 2018, Advance Article
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    Selective access to dipyrazolo-fused pyridines via formal [3 + 2 + 1] heteroannulation of methyl ketones with pyrazol-5-amines

    Q. Gao, S. He, X. Wu, J. Zhang, S. Bai, Y. Wu and A. Wu, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00941K

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