Collect. Czech. Chem. Commun. 1987, 52, 2971-2982

Crown and azacrown ethers with pendant adenine group

Petr Holý, Martin Bělohradský, Ivan Stibor, Juraj Koudelka, David Šaman, Jana Hodačová, Antonín Holý and Jiří Závada

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Base-catalyzed oxirane ring-opening reaction of 4,5-epoxy-2-oxapentyl crown ethers Ia-Ie and N-(2,3-epoxy-1-propyl) azacrown ethers IIa-IIc with adenine affords mixtures of corresponding adenin-9-yl, adenin-3-yl and adenin-7-yl derivatives (IIIa-IIIe, IVa-IVe, Va-Ve, VIa-VIc, VIIa-VIIc and VIIIa-VIIIc) respectively, separable by liquid chromatography. Structure of the individual isomers was assigned on basis of 1H, and 13C NMR spectroscopy. Compexation of the prevailing (adenin-9-yl) isomers IIIa-IIIe and VIa-VIc with sodium ion was measured potentiometrically in 99% methanol and the calculated stability constants were compared with corresponding data from related homologous series of crown and azacrown ethers IXa-IXe, Xa-Xe, XIa-XIc and XIIa-XIIc differing in pendant group.