Synthesis and transformations of alkyl 1,5-bis(dimethylamino)-3-oxopenta-1,4-diene-2,4-dicarboxylates. A simple synthesis of dialkyl 1-substituted 4-oxo-1,4-dihydropuridine-3,5-dicarboxylates
S. Zupancic et al., Synthesis and transformations of alkyl 1,5-bis(dimethylamino)-3-oxopenta-1,4-diene-2,4-dicarboxylates. A simple synthesis of dialkyl 1-substituted 4-oxo-1,4-dihydropuridine-3,5-dicarboxylates, HETEROCYCLE, 53(9), 2000, pp. 2033-2042
Dimethyl (2a) and diethyl 1,5-bis(dimethylamino)-3-oxo-penta-1,4-diene-2,4-
dicarboxylate (2b), available in good yields from the corresponding dialkyl
acetonedicarboxylates (1a, b) and N,N-dimethylformamide dimethyl acetal (D
MFDMA), were used as reagents for a one-step preparation of 1-substituted 1
,4-dihydropyridin-4-ones (3a-u). Thus, compounds (2) were treated with ammo
nia, hydrazines, and primary aliphatic, aromatic, or heterocyclic amines to
form dialkyl 1-substituted 4-oxo-1,4-dihydropyridine-3,5-dicarboxylates (3
a-u).