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Issue 23, 2012
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Synthesis of diversely 1,3,5-trisubstituted pyrazolesvia 5-exo-dig cyclization

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Abstract

5-Exo-dig cyclocondensation of alk-3-yn-1-ones with hydrazines, in the presence of montmorillonite K-10, provides an effective method with a high atom economy for the synthesis of diversely 1,3,5-trisubstituted pyrazoles. The microwave-accelerated reaction proceeds in the absence of solvent and leads to 5-benzyl substituted pyrazoles with good yields (72–91%). The regiochemistry of the process was confirmed by the X-ray crystallographic structure determination of 1-(2-fluorophenyl)-5-(4-methylbenzyl)-3-phenyl-1H-pyrazole.

Graphical abstract: Synthesis of diversely 1,3,5-trisubstituted pyrazoles via 5-exo-dig cyclization

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Publication details

The article was received on 18 Mar 2012, accepted on 01 May 2012 and first published on 10 May 2012


Article type: Communication
DOI: 10.1039/C2OB25580D
Org. Biomol. Chem., 2012,10, 4505-4508

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    Synthesis of diversely 1,3,5-trisubstituted pyrazoles via 5-exo-dig cyclization

    D. A. Borkin, M. Puscau, A. Carlson, A. Solan, K. A. Wheeler, B. Török and R. Dembinski, Org. Biomol. Chem., 2012, 10, 4505
    DOI: 10.1039/C2OB25580D

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