Synthesis and NMR properties of the first boron analogues of uracil

Synthesis of 4-hydroxyborauracil and 4-hydroxy-3-methylborauracil, the first boron analogues of uracil, and comparison of their 1H and 13C NMR properties with those of uracil, are presented. The analyses of NMR-monitored boron compound–alcohol and boron compound–amine interactions pointed to the existence of sp3-hybridized, B,B-bis-methoxyborauracils and pyridine-/n-butylamine-borauracils ate-complexes in solution.

Graphical abstractSynthesis of 4-hydroxyborauracil and 4-hydroxy-3-methylborauracil, the first boron analogues of uracil, and comparison of their 1H and 13C NMR properties with those of uracil, are presented. The analyses of NMR-monitored boron compound–alcohol and boron compound–amine interactions pointed to the existence of sp3-hybridized, B,B-bis-methoxyborauracils and pyridine-/n-butylamine-borauracils ate-complexes in solution.Figure optionsDownload full-size imageDownload as PowerPoint slide