ChemInform Abstract: Reactions of β-Bromo-N-heteroaromatics with Phenylacetonitrile

The reaction of 3-bromopyridine with phenylacetonitrile in the presence of NaH in THF gave a simple substitution product, α-phenyl-3-pyridineacetonitrile, whereas the reaction of 5-bromopyrimidine with phenylacetonitrile under similar conditions gave a ring-transformation product, 2-amino-5-bromo-3-phenylpyridine. 3-bromoquinoline and 4-bromoisoquinoline underwent the former type reaction, while 3-bromo- and 3-chloroisoquinolines were converted into 2-amino-3-phenyl-1-naphthalencarbonitrile according to the latter type reaction