Studies on #beta#- enaminonitriles: Part IV-Reaction of #beta#-enaminonitriles with acid chlorides

摘要

Acylation of #beta#-aminocrotononitrile with saturated acid chlorides in the presence of pyridine produces highly contrasting results. Thus, acylation with saturated straight-chain aliphatic acid chlorides shows exclusive preference for C-arylation whereas branched-chain acid chlorides shows a complete reversal of site selection giving only the corresponding N-acylated products. However, with aromatic acid chlorides no such clear-cut preference for regioselective has been observed. The position as well as the nature of the substituents are found to be critical in determining the site of acylation. With heteroaromatic acid chlorides the regioselection is found to be dependent on the nature of the heteroatoc present in the ring.