Collect. Czech. Chem. Commun. 1994, 59, 1841-1852

Cyclization Dichotomy of Esters of 3-Ureido-2-cyano-2-propenoic and 3-Ureido-2-acyl-2-propenoic Acids

Miroslav Ledvina and Jiří Farkaš

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The preparation of E and Z isomers of 3-ureido-2-cyano-2-propenoates Ia - Id and their base-catalyzed isomerization and cyclization to 5-carboxycytosine derivatives IIa - IIf and 5-cyanouracil derivatives IIIa and IIIb is described. Also described is the preparation of 3-ureido-2-acyl-2-propenoates Va - Vd and their base-catalyzed cyclization to 5-carboxy-2(1H)-pyrimidone derivatives VIa - VIc and 5-acyluracils VIIa - VIIc.