2(5H)-FURANONE IN THE VILSMEIER–HAAK REACTION. SYNTHESIS OF β-SUBSTITUTED FURANS. MOLECULAR STRUCTURES OF 3-DIMETHYLAMINOMETHYLENE-5-FORMYL-2(3H)-FURANONE AND DIMETHYLAMMONIUM3,5-DI(2,2-DIMETHYL-4,6-DIOXO-1,3-DIOXAN-5-YLIDENEMETHYL)-2-FURANOLATE

Abstract

The reaction of 2(5H) furanone with the Vilsmeier–Haak–Arnold reagent and subsequent addition of concentrated aqueous HClO4 to the reaction mixture give (3-dimethylaminomethylen-2-oxo-3H-5-furanyl)methylenimmonium perchlorate, whose hydrolysis under various conditions leads to 3-dimethylaminomethylene-5-formyl-2(3H)-furanone or to the potassium salt of 5-hydroxy-2,4-furandicarbaldehyde. The reaction of these products with CH acids was studied. The structures of the key compounds of this work have been proved by the method of X ray diffraction analysis.

Authors: G. D. Krapivin, N. D. Kozhina, L. A. Chernousenko, and V. E. Zavodnik.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (1), pp 23-32

http://link.springer.com/article/10.1007/BF02251656