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

Citation
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
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
9
Year of publication
2000
Pages
2033 - 2042
Database
ISI
SICI code
0385-5414(20000901)53:9<2033:SATOA1>2.0.ZU;2-D
Abstract
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).