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■ 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-dihydropyridine-3,5-dicarboxy-lates

Silvo Zupancic, Jurij Svete,* and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia

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 (DMFDMA), 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 ammonia, hydrazines, and primary aliphatic, aromatic, or heterocyclic amines to form dialkyl 1-substituted 4-oxo-1,4-dihydropyridine-3,5-dicarboxylates (3a-u).