Collect. Czech. Chem. Commun. 1984, 49, 2496-2501

Preparation of 5-X-2-(2-nitrovinyl)furans and their reactions with nucleophiles

Rudolf Kada, Viera Knoppová, Jaroslav Kováč and Irena Maleňáková

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


The title compounds were prepared by condensation of 5-X-2-furaldehydes (X = H, Br, C6H5S, C6H5SO2, 4-CH3-C6H4SO2, 3-O2N-C6H4O) with nitromethane in methanol. 5-Trimethylammonium-2-(2-nitrovinyl)furan bromide (Ii) was obtained from 5-bromo-2-(2-nitrovinyl)furan (Ib) and trimethylamine in benzene; its thermal decomposition in methanol furnished 5-dimethylamino-2-(2-nitrovinyl)furan (Ih). Reactions of 5-X-2-(2-nitrovinyl)furans with nitrogen-containing nucleophiles were investigated.