The reaction of 2‐dimethylaminomethylene‐3‐oxo‐ N ‐phenylbutyramide with active methylene nitriles

2‐Dimethylaminomethylene‐3‐oxo‐ N ‐phenylbutyramide 1 reacts with malononitrile 2a to afford the pent‐2‐enedioic acid 1‐amide 5‐phenylamide derivative 6 , which could be cyclized to give the 6‐methylpyridone derivative 7 . Compound 1 reacts with cyanoacetamide 2b to afford the same pyridone 7 and with cyanothioacetamide 2c to afford the analogous pyridinethione 12 . Compound 12 reacts with DMAD to afford the pyridine derivative 15 and with N,N ‐dimethylchloroacetamide 16 to afford the thieno[2,3‐d]pyridine derivative 18 . Compound 18 reacts with morpholine‐4‐carboxaldehyde 19 , N,N ‐diemthylformamide 20 , and 2,5‐dimethoxy‐tetrahydrofuran 21 to afford the fully aromatic thieno[2,3‐d]pyridine derivatives 22 , 23 , and 24 , respectively. J. Heterocyclic Chem., (2010).