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

Organic & Biomolecular Chemistry
Dmitry A BorkinRoman Dembinski

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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Citations

Jan 29, 2020·Chemistry : a European Journal·Jose S S Neto, Gilson Zeni
Jan 15, 2013·Organic & Biomolecular Chemistry·Hyejin ChoBéla Török
Jan 28, 2020·Current Organic Synthesis·Anne KokelBéla Török
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Denisa DumitrescuFlorea Dumitrascu
Oct 28, 2021·Molecular Diversity·Thangapandi Chellapandi, Gunabalan Madhumitha

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