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, l-(β-d-ribofuranosyl)-4,6-bis(polyfluoroalkyl)-1H-pyrazolo[3,4-d]pyrimidines were prepared starting from iso-AIRs.

Iaroshenko V. O.
Synthesis 2009, 23, 3967-3974
DOI: 10.1055/s-0029-1217015