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Synthesis 2013; 45(3): 413-420
DOI: 10.1055/s-0032-1317992
DOI: 10.1055/s-0032-1317992
paper
An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes
Further Information
Publication History
Received: 08 November 2012
Accepted after revision: 13 December 2012
Publication Date:
09 January 2013 (online)
Abstract
A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and gem-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3H-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1H-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient substituents on the aromatic ring of the hydrazones or the gem-dibromoalkenes gave desired products in moderate to good yields (67–86%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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