Collect. Czech. Chem. Commun. 1983, 48, 1057-1061

Phenylsulfonyl derivatives of chalcones derived from 5-nitrofuran

Adolf Jurášek, Dana Polakovičová and Jaroslav Kováč

Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava


1-(5-Nitro-2-furoyl)-1-phenylsulfonyl-2-(4-X-phenyl)ethylenes II were synthesized by condensation of phenyl-2-(5-nitro-2-furyl)-2-oxoethyl sulfone (I) with 4-substituted benzaldehydes (X = H, CH3, CH3O, N(CH3)2, F, Cl, NO2, CN) in tetrahydrofuran or dioxane under catalysis of titanium-IV chloride and pyridine. As evidenced by spectral data (1H NMR, IR, UV) the stereospecific condensation afforded exclusively Z isomers of ethylenes II; these exist in an 0,0-trans, s-cis conformation.