Synthesis of glycosides of 1H-Pyrazolo[3,4-b]pyridin-3(2H)-ones

Abstract A number of new fluorinated and non-fluorinated glycosides of 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were synthesized by direct attachment of the carbohydrate moiety to the heterocycle using the silyl Hilbert-Jones glycosylation method. The products were obtained in good to excellent yields and with very good anomeric stereoselectivity. The starting 1H-pyrazolo[3,4-b]pyridin-3(2H)-ones were prepared by regioselective cyclization of 1,3-dicarbonyl compounds with electron-rich heterocycles containing an enamine functionality.