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Domino reaction of a gold catalyzed 5-endo-dig cyclization and a [3,3]-sigmatropic rearrangement towards polysubstituted pyrazoles†
Arno Verlee,Thomas Heugebaert,Tom van der Meer,Pavel Kerchev,Frank Van Breusegem,Christian V. Stevens
Organic & Biomolecular Chemistry Pub Date : 11/28/2018 00:00:00 , DOI:10.1039/C8OB02807A
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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