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Issue 48, 2018
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Domino reaction of a gold catalyzed 5-endo-dig cyclization and a [3,3]-sigmatropic rearrangement towards polysubstituted pyrazoles

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Abstract

Pyrazoles are important heterocyclic compounds with a broad range of biological activities. A new procedure toward tri- or tetrasubstituted pyrazoles has been developed, via a one-pot gold catalyzed synthesis from hydrazines with alkynyl aldehydes or ketones. The reaction proceeds through consecutive hydrazone formation, 5-endo-dig cyclization and an aza-Claisen rearrangement resulting in the desired polysubstitued pyrazoles.

Graphical abstract: Domino reaction of a gold catalyzed 5-endo-dig cyclization and a [3,3]-sigmatropic rearrangement towards polysubstituted pyrazoles

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Article information


Submitted
10 Nov 2018
Accepted
28 Nov 2018
First published
28 Nov 2018

Org. Biomol. Chem., 2018,16, 9359-9363
Article type
Communication

Domino reaction of a gold catalyzed 5-endo-dig cyclization and a [3,3]-sigmatropic rearrangement towards polysubstituted pyrazoles

A. Verlee, T. Heugebaert, T. van der Meer, P. Kerchev, F. Van Breusegem and C. V. Stevens, Org. Biomol. Chem., 2018, 16, 9359
DOI: 10.1039/C8OB02807A

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