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Issue 29, 2017
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Copper(I) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles

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Abstract

Herein, a two-step MCR-oxidation methodology accessing decorated 2° α-ketoamides and α-ketotetrazoles is described via a catalytic copper(I)-mediated C–N oxidation/acidic hydrolysis of Ugi-three-component and Ugi-azide reaction products. The ability to install diversity from aldehyde and isocyanide synthons allows rapid complexity generation. Of note, (1) 2° α-ketoamides are traditionally difficult to access and more so reminiscent of the endogenous peptide bonds. (2) The route to α-keto-tetrazoles is significantly shorter than that in previous reports.

Graphical abstract: Copper(i) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles

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Publication details

The article was received on 09 Apr 2017, accepted on 29 Jun 2017 and first published on 29 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB00881C
Citation: Org. Biomol. Chem., 2017,15, 6132-6135
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    Copper(I) catalyzed oxidative hydrolysis of Ugi 3-component and Ugi-azide reaction products towards 2° α-ketoamides and α-ketotetrazoles

    J. W. Collet, C. Foley, A. Y. Shaw, R. V. A. Orru, E. Ruijter and C. Hulme, Org. Biomol. Chem., 2017, 15, 6132
    DOI: 10.1039/C7OB00881C

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