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

• Published in: Synthesis (Stuttgart) 2013-02, Vol.45 (3), p.413-420
• Main Authors: Sha, Qiang, Wei, Yunyang
• Format: Article
• Language: English
• ISSN: 0039-7881; 1437-210X
• DOI: 10.1055/s-0032-1317992

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-3 H -pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1 H -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%).