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

AI Article Synopsis

  • A method has been developed for synthesizing 1,3,5-trisubstituted pyrazoles using the 5-exo-dig cyclocondensation of alk-3-yn-1-ones with hydrazines, utilizing montmorillonite K-10 as a catalyst.
  • This reaction is efficient, boasting high atom economy, and can be carried out without any solvent, with microwave acceleration for faster results.
  • Good yields (72-91%) of 5-benzyl substituted pyrazoles were achieved, and the structure of one specific compound was confirmed using X-ray crystallography.

Article 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.

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Source
http://dx.doi.org/10.1039/c2ob25580dDOI Listing

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