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Paper | Special issue | Vol 50, No. 2, 1999, pp.853-866
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)81
Ethyl 2-(2-Acetyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoate in the Synthesis of Heterocyclic Systems. The Synthesis of Substituted 3-Aminoazolo- and -azinopyrimidinones, Pyridopyridinones and Pyranones

Renata Toplak, Mitja Zucchiati, Simona Golic Grdadolnik, and Branko Stanovnik*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia


Ethyl 2-(2-acetyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoate (2) was prepared from ethyl N-(2-acetyl-2-ethoxycarbonyl-1-ethenyl)glycynate (1) and N,N-dimethylformamide dimethyl acetal, and used as a reagent for preparation of substituted amino azolo- and azinopyrimidin-4-ones (16-20), quinolizin-4-ones (31 and 32 ), 2H-1-benzopyran-2-ones (33), and isomeric naphthopyranones (34-37), 2H-pyrano[2,1-b]pyridine-2,5-dione (38), pyrano[4,5-b]pyran-2,5-dione (39) and pyrano[3,2-c]bezopyran-2,5-dione (40).