Interaction of α-bromoacetylphenylacetonitrile with some N- and S-nucleophiles

4-Dialkylamino-3-hydroxy-2-phenyl-2-butenonitriles were obtained by interaction of α-bromoacetylphenylacetonitrile with aliphatic (including cyclic) secondary amines. Analogous interaction with dibenzylamine and N-ethylaniline accompanied by the dealkylation leads to 1-benzyl- and 1-phenyl-5-amino-4-phenyl-2,3-dihydro-1H-3-pyrrolones. Depending on the conditions of hydrolysis, butenonitriles were converted into corresponding amides or, as a result of tertiary amino group cleavage, to 1-alkyl-5-amino-4-phenyl-2,3-dihydro-1H-3-pyrrolones. When being alkylated with α-bromoacerylphenylacetonitrile, the thiols afforded the corresponding thioesters.