Studies on Heterocyclic Enaminonitriles. IX. : Ring Openiong of 2-Amino-3-cyano-4, 5-dihydrofurans by the Use of Benzoyl(and Acetyl) Chlorides

Abstract

The reaction of 2-amino-3-cyano-4, 5-dihydrofuran (Ia) with benzoyl(or acetyl) chloride in the presence of sodium hydride and sodium hydrogen carbonate gave 2-benzoyloxy(or acetoxy)ethyl-malononitrile (IIa or IIIa). Similarly, 2-amino-3-cyano-5-methyl-4, 5-dihydrofuran (Ib) and 2-amino-3-cyano-4-phenyl(or 5-phenyl)-4, 5-dihydrofuran (Ic or Id) reacted with benzol(or acetyl)-chloride to form the corresponding malononitrile derivatives (IIb-d or IIIb-d). On the other hand, the reaction of Ia with phenacyl bromide gave 3-cyano-2-imino-3-phenacyltetrahydrofuran (IV).