Collect. Czech. Chem. Commun.
1994, 59, 444-452
https://doi.org/10.1135/cccc19940444
Synthesis, Reactions and Spectral Properties of Ethyl Esters of 2-Cyano-3-(5-X-2-furyl)acrylic Acid
Rudolf Kadaa, Dušan Ilavskýa, Jarmila Štetinováa, Lubomír Zaliberab and Jiří Paďoura
a Department of Organic Chemistry, Slovak Technical University, 812 37 Bratislava, Slovak Republic
b Department of Physical Chemistry, Slovak Technical University, 812 37 Bratislava, Slovak Republic
Abstract
The reaction of 5-X-2-furaldehydes (X = C6H5, COOCH3, COOC2H5, C6H5O, C6H5S, CH3S, 4-Cl-C6H4S, CH3SO2, C6H5SO2, 4-Cl-C6H4SO2) with ethyl cyanoacetate in dry ethanol catalyzed by sodium ethoxide yielded the corresponding ethyl 2-cyano-3-(5-X-2-furyl)acrylates. It was found that the reactions of these esters with cyanoacetophenone or ethyl acetoacetate do not afford the corresponding 4H-pyran derivatives but that there proceeds the exchange of ethyl acetoacetate or of ethyl cyanoacetate for the cyanoacetophenone carbanion. The same course has been observed also for the reactions of these substrates with malononitrile.
