Reaction of dianions of acyclic .beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives

Abstract

A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of β-(monoalkylamino)-α,β-unsaturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both α'- and γ-dianions which are regioselectively generated. The reaction of γ-dianions with nitriles is strongly influenced by temperature. The γ-addition products cyclize to 4-aminopyridines when the reaction is run below -50 o C