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Paper | Regular issue | Vol 55, No. 4, 2001, pp.705-727
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9150
Reactions of Alkyl (Z)-2-[(E)-2-Cyano-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates with C- and N-Nucleophiles. The Synthesis of Fused 2H,5H-Pyran-2,5-diones, 4H-Pyrimidin-4-ones, and 1-Heteroaryl-1H-imidazole-4-carboxylates

Lucija Jukic, Jurij Svete,* and Branko Stanovnik*

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


Alkyl (Z)-2-[(E)-2-cyano-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates (2) and (3) were transformed with C- and N-nucleophiles into alkyl 2-[2-cyano-2-(2-pyridinyl)ethenyl]amino-3-heteroarylpropenoates (10-13), 2H,5H-benzo[b]pyran-2,5-diones (14) and (15), 2H,5H-pyrano[4,3-b]pyran-2,5-dione (16), 2H,5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione (17), alkyl 2-[2-cyano-2-(2-pyridinyl)ethenyl]amino-3-arylamino- (28-40), and 3-heteroarylaminopropenoates (41-43), pyrido[1,2-a]pyrimidin-4-ones (50-53), thiazolo[3,2-a]pyrimidin-4-one (54), benzothiazolo[3,2-a]pyrimidin-4-one (55), and 1-heteroaryl-1H-imidazole-4-carboxylate (56). Compounds (28-43) exist in (2E, 2’E) form or as a mixture of (2E, 2’E) as a major and (2Z,2’E) form as a minor isomer.