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Issue 12, 2012
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Copper-catalyzed oxidative [2 + 2 + 1] cycloaddition: regioselective synthesis of 1,3-oxazoles from internal alkynes and nitriles

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Abstract

A robust and regioselective copper(II)-catalyzed cycloaddition of internal alkynes and nitriles providing an effective access to oxazole fragments is reported herein. Water substantially participated in this reaction. Control experiments proposed that this transformation may proceed via an enamide intermediate. This strategy enables the preparation of the core structure of a COX-2 inhibitor.

Graphical abstract: Copper-catalyzed oxidative [2 + 2 + 1] cycloaddition: regioselective synthesis of 1,3-oxazoles from internal alkynes and nitriles

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Publication details

The article was received on 22 Jul 2012, accepted on 29 Aug 2012 and first published on 30 Aug 2012


Article type: Edge Article
DOI: 10.1039/C2SC21041J
Citation: Chem. Sci., 2012,3, 3463-3467
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    Copper-catalyzed oxidative [2 + 2 + 1] cycloaddition: regioselective synthesis of 1,3-oxazoles from internal alkynes and nitriles

    X. Li, L. Huang, H. Chen, W. Wu, H. Huang and H. Jiang, Chem. Sci., 2012, 3, 3463
    DOI: 10.1039/C2SC21041J

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