Abstract

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.

摘要

在这项研究中，据报道通过点击反应合成了十二种核苷类似物。首次通过不同途径合成了D-吡喃葡萄糖、D-吡喃半乳糖、D-呋喃核糖和2-炔丙基氨基嘧啶衍生物( 5和7 )的叠氮衍生物之间的反应。第一步，1H-吡唑-1-甲脒盐酸盐与炔丙胺反应得到N-炔丙基胍，然后N-炔丙基胍与β-二酮（4和6）缩合得到2-炔丙基氨基嘧啶(5和7 ) 首次获得良好的收益率 (85%)。最后，用叠氮糖 ( 8a-8f ) 和 2-炔丙基氨基嘧啶衍生物进行点击反应，并以良好的收率产生了十二种新的核苷类似物。（9a-9f、10a-10f、65-73% 产率）。新衍生物的化学结构已通过光谱技术阐明，例如 FT-IR、¹ H NMR、¹⁹ F NMR、¹³ C NMR 和 TOF-ESI-MS。