Collect. Czech. Chem. Commun. 1983, 48, 1885-1890

Synthesis and reactions of trimethylammonium salts of 5-nitro-2-furan and 5-nitro-2-thiophene. The preparation of 5-nitro-2-furyl- and 5-nitro-2-thienyl azide

Daniel Végh, Jaroslav Kováč and Miloslava Dandárová

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


Preparation of new water-soluble derivatives of 5-nitro-2-furan and 5-nitro-2-thiophene from 2-bromo-5-nitrofuran (Ia) or 2-bromo-5-nitrothiophene (Ib) and trimethylamine is described. The trimethylammonium derivatives IIa, IIb react with the azide or cyanide anion in water to afford azides IVa, IVb or nitriles Va, Vb of 5-nitro-2-furan or 5-nitro-2-thiophene. The reactivity of these azides with dimethyl 2-butinedioate and triphenyl phosphine was studied.