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Issue 33, 2012
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Au(I)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines

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Abstract

Pyrazolo[1,5-a]pyridines and 6-iodopyrazolo[1,5-a]pyridines were synthesized by gold-catalyzed and iodine-mediated cyclization of enynylpyrazoles in good to excellent yields, respectively. The iodinated adducts were further converted to 6-arylpyrazolo[1,5-a]pyridines via Suzuki–Miyaura coupling reaction and 6-cyanopyrazolo[1,5-a]pyridine by Ullmann condensation reaction. One of the cyclization adducts, 2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine, was converted to a p38 kinase inhibitor, 2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine, in two steps.

Graphical abstract: Au(i)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines

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Publication details

The article was received on 21 May 2012, accepted on 27 Jun 2012 and first published on 28 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25973G
Citation: Org. Biomol. Chem., 2012,10, 6640-6648
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    Au(I)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines

    H. Wu, C. Yang, L. Hwang and M. Wu, Org. Biomol. Chem., 2012, 10, 6640
    DOI: 10.1039/C2OB25973G

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