An acid catalyzed one-pot condensation of readily available cyclic β-diketones, arylglyoxals and arylhydrazones produces a library of diversely functionalized pyrazole derivatives in excellent yield under metal-catalyst-free benign conditions.
A one-pot, three-component, and atom economic synthesis of biologically and pharmaceutically important fully substituted and functionalized pyrazole derivatives has been accomplished under metal-catalyst-free benign conditions. The strategy involves early condensation of readily available cyclic β-diketones (dimidone, 4-hydroxycoumarin and 2-hydroxy-1,4-naphthoquinone) and arylglyoxals to generate a chalcone type intermediate which upon acid catalyzed condensation with ambident nucleophile arylhydrazones produces various aryl and cyclic β-diketone substituted pyrazole derivatives. The synthesis embraces high functional group tolerance, broad substrate scope, excellent yield of the products, short reaction time and operationally simple and mild reaction conditions. The synthesis provides an easy opportunity of incorporating biologically important N-diarylsulfide/selenide functionality, various enolisable cyclic β-diketones and other bioactive heterocycles concurrently to pyrazole, which may help in designing and development of pyrazole derivatives of pharmacological significance.Zum Volltext