ACETALS OF LACTAMS AND ACID AMIDES. 53. ENAMIDINES IN THE SYNTHESIS OF PYRIDINE AND PYRIMIDINE

Article abstract of DOI:10.1007/BF00479349

The reaction of α-cyano-β-aminocrotonic ester with DMFA diethylacetal gives 1-ethoxycarbonyl-1-cyano-2-(N-dimethylaminomethylene)-amino-4-dimethylaminobutadiene, the reaction of which with ammonium acetate and amines leads to 4-methylenepyrimidine derivatives.Condensation of α-cyano-β-aminocrotonic ester with dimethylacetamide diethylacetal gave 2-(ethoxycarbonylcyano)methylene-4-dimethylamino-6-methylpyridine.It was found that in an alkaline medium, 1-benzyl-4-(ethoxycarbonylcyano)methylenepyrimidine recyclizes into 1-benzyl-3-cyano-4-amino-2-pyridone.