Preparation and NMR study of 7,7'-(α,ω-alkanediyl)bis[theophylline], 1,1'-(α,ω-alkanediyl)bis[theobromine], and 1,1'-(α,ω-alkanediyl)bis[3-methyluracil]

Article abstract of DOI:10.1246/bcsj.67.203

The treatment of theophylline, theobromine, and 3-methyluracil with X(CH₂)(n)X (X = Br or I, n = 1-12) in N,N-dimethylformamide containing sodium hydride gave the corresponding 7,7'-(α,ω-alkanediyl)bis[theophylline], 1,1'-(α,ω-alkanediyl)bis[theobromine], and 1,1'-(α,ω-alkanediyl)bis[3-methyluracil]. The interaction of the theophylline, theobromine, and 3-methyluracil rings of these compounds was studied based on their ¹H NMR spectra, and stacking of the two purine rings of 7,7'-(α,ω-alkanediyl)bis[theophylline] was observed.