Designing new isomorphic fluorescent nucleobase analogues: the thieno[3,2-d]pyrimidine core

A convergent approach for a family of fluorescent nucleosides is described. It relies on thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione that serves as a core heterocycle. This condensed pyrimidine is converted into an emissive pyrimidine nucleoside analogue by N-glycosylation and into an emissive purine nucleoside analogue by C-glycosidation at the thiophene's beta position. The design principles of this archetypical system are outlined together with the syntheses and photophysical properties of the resulting nucleosides.