Synthesis of Some Fluorinated Heteroannulated Pyrimidines, Purine Isosteres, via Inverse-Electron-Demand Diels-Alder Protocol

The inverse-electron-demand Diels-Alder reaction of electron excessive systems such as enamines, electron-enriched amino heterocycles, and anilines with 2,4,6-tris(polyfluoroalkyl)-1,3,5-triazines was investigated. This study results in the synthesis of a set of polyfluoroalkyl containing pyrimidines, heteroannulated pyrimidines, and quinazolines. Following the elaborated synthetic pathway, 1-(beta-D-ribofuranosyl)-4,6-bis(polyflitoroalkyl)-1H-pyrazolo[3,4-d]pyrimidines were prepared starting from iso-AIRs.