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 1 H -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, 1 H NMR, 19 F NMR, 13 C NMR and TOF-ESI-MS.