Reactions of Substituted Furan-2,3-diones with C- and N-Nucleophiles

Abstract

The thermolysis of 5-phenyl-2,3-dihydrofuran-2,3-dione in 4-methoxyphenylacetone yield 2-(4-methoxybenzyl)-2- methyl-6-phenyl-4H-1,3-dioxin-4-one via α-oxoketene. Reaction of 5-phenyl-2,3-dihydrofuran-2,3-dione with phenylhydrazine afforded 1,6-diphenyl-1,2-dihydropyridazine- 3,4-dione. The hydrazine derivatives and 1,2-phenylenediamine react with 4,4-dimethyltetrahydrofuran-2,3-dione to give the corresponding hydrazone derivatives and 3,3- dimethyl-2,3-dihydrofuro[2,3-b]quinoxaline, respectively. The structures of compounds were characterized on the basis of elemental analyses, Mass, IR, ¹H and ¹³C NMR spectra.