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Synthesis 2015; 47(13): 1877-1886
DOI: 10.1055/s-0034-1379906
DOI: 10.1055/s-0034-1379906
paper
Catalyst-Free and Oxidant-Free Synthesis of 1,3,5-Trisubstituted Pyrazoles by Michael-Type Addition of Hydrazone sp2 Nitrogen Atoms to Enones
Further Information
Publication History
Received: 28 December 2014
Accepted after revision: 05 March 2015
Publication Date:
31 March 2015 (online)
Abstract
A new single-step approach to 1,3,5-trisubstituted pyrazoles from hydrazones and α,β-unsaturated keto esters has been developed. This catalyst- and oxidant-free transformation involves a Michael-type addition of the hydrazone sp2 nitrogen to the enone and a redox isomerization. The procedure has a wide substrate scope and shows good compatibility with both α-ester- and α-keto-substituted hydrazones.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379906.
- Supporting Information
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For selected patents, see:
For reviews, see:
For recent examples of syntheses of pyrazoles, see:
For examples, see: