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Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

Essmat M. El-Sheref, Ashraf A. Aly, Aboul-Fetouh E. Mourad, Alan B. Brown, Stefan Bräse, and Momtaz E. M. Bakheet

Minia University, El-Minia, Egypt

 

E-mail: ashrafaly63@yahoo.com

Abstract: Reaction of equimolar amounts of 2,4(1H,3H)-quinolinediones and diethyl acetylenedicarboxylate in absolute ethanol, containing catalytic triethylamine, gave ethyl 5,6-dihydro-2,5-dioxo-6,9-disubstituted-2H-pyrano[3,2-c]quinoline-4-carboxylates in good yields. In a different manner, reaction of two equivalents of dialkyl acetylenedicarboxylates with one equivalent of 2,4(1H,3H)-quinolinediones afforded dialkyl 2(4-oxo-1,4-dihydroquinolin-3-yl)fumarates in good yields. The structures of the products were elucidated by 1H NMR, 13C NMR, two-dimensional NMR, IR, mass spectra and elemental analyses.

Keywords: 2,4(1H,3H)-Quinolinediones ; Dialkyl acetylenedicarboxylates ; Pyrano[3,2-c]quinolones ; Quinolinofumarates 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0269-6

 

Chemical Papers 72 (1) 181–190 (2018)

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