Efficient synthesis of new biheterocyclic 1-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-3-(6-trifluoro methylpyrimidin-4-yl)-propan-1-ones

•Use of renewable precursor, levulinic acid.•Easy diversification of products derived from the change of dinucleophiles.•The route proposed allows to obtain systems with two trifluoromethylated heterocycles.•The products obtained are all unpublished and with potential CNS activity.

Several new 1-(5-hydroxy-5-trifluoromethyl-1H-pyrazol-1-yl)-3-(6-trifluoromethyl pyrimidin-4-yl)-propan-1-ones were prepared by cyclocondensation between two different 3-[6-trifluoromethyl-2-(substituted)pyrimidin-4-yl]propanoylhydrazides derived from levulinic acid and versatile 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones. The structure of new propionyl-spaced bis trifluoromethylated biheterocycles was characterized based on 1H and 13C nuclear magnetic resonance spectroscopy and mass spectrometry data.

Graphical abstractCyclocondensation between two different 3-[6-trifluoromethyl-2-(substituted)pyrimidin-4-yl]propanoylhydrazides derived from levulinic acid and versatile 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones.Figure optionsDownload full-size imageDownload as PowerPoint slide