Synthesis of new 1,2,3-triazolo-nucleoside analogues with 2-propargylamino pyrimidines via click reactions

In this study, it was reported that twelve nucleoside analogues were synthesized by click reactions. The reactions were carried out between the azide derivatives of D-glucopyranose, D-galactopyranose, D-ribofuranose and 2-propargylamino pyrimidine derivatives (5 and 7) that are synthesized via a different route for the first time. In the first step, N-propargyl guanidine was obtained with the reaction of 1H-pyrazole-1-carboxamidine hydrochloride and propargyl amine, then condensation of N-propargyl guanidine and β-diketone (4 and 6) resulted in 2-propargylamino pyrimidines (5 and 7) for the first time in good yields (85%). Finally, click reactions were performed with azidosugars (8a-8f) and 2-propargylamino pyrimidine derivatives and produced twelve new nucleoside analogues in good yields. (9a-9f, 10a-10f, 65-73% yields). The chemical structures of the new derivatives were elucidated spectroscopic techniques, such as FT-IR, ¹H NMR, ¹⁹F NMR, ¹³C NMR and TOF-ESI-MS.