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Paper | Regular issue | Vol 45, No. 3, 1997, pp.555-565
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7713
Reactions of Ethyl (Z)-2-[2,2-Bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate with C-Nucleophiles. Synthesis of Substituted 3-Amino-2H-pyran-2-ones

Renata Toplak, Lovro Selic, Gorazd Sorsak, and Branko Stanovnik*

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

Abstract

The reactions of ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate (1) with C-nucleophiles, such as β-keto esters (2, 4, 6), cyclic 1,3-diketones (8a-e), aromatic hydroxy compounds (10, 12, 14, 16 and 18), and heterocyclic hydroxy compounds (20, 22, 24, 26 and 28) gave 2H-pyran-2-ones (3, 5, 7), tetrahydrobenzopyranones (9a-c), benzopyranone (11), naphthopyranones (13, 15, 17 and 19), pyranopyranone (21), pyranobenzopyranone (23), pyranopyridinone (25), pyranoquinolinone (27), and pyranopyridazinone (29) derivatives.