Abstract
Malononitrile reacts with 2-chloroethanol and 1-chloro-2-propanol (or 2-methyloxirane) in the presence of sodium ethoxide to give 2-amino-3-cyano-4, 5-dihydrofuran (Ia) and 2-amino-3-cyano-5-methyl-4, 5-dihydrofuran (Ib), respectively. The reaction of malononitrile with 2-phenyl-oxirane or 2-chloro-1-phenylethanol gave 2-amino-3-cyano-4 (and 5)-phenyl-4, 5-dihydrofurans (Ic and Id). The 2-benzamido derivatives (IIb-d) of Ib-d were aromatized by treatment with N-bromosuccinimide to give the corresponding furans (IIIb-d).
