Catalyst-Free Regio-and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofurant  

作　　者：Xiaodong Gu Qingwei Du Weijian Song Jun(Joelle)Wang 

机构地区：[1]Department of Chemistry,Hong Kong Baptist University,Kowloon,Hong Kong,China [2]Department of Chemistry,Southern University of Science and Technology,Shenzhen,Guangdong 518055,China

出　　处：《Chinese Journal of Chemistry》2023年第2期167-172,共6页中国化学（英文版）

基　　金：We gratefully acknowledge HKBU RC-Tier 2 Start-up Grant for financial support.

摘　　要：An efficient and practical synthesis of heterocyclic nucleosides is developed by a catalyst-free highly regioselective and diastereose-lective[3+2]annulation of a-purine-substituted acrylates with nitrones.The reaction operates with excellent functional group toler-ance,very mild reaction conditions,and with the green,sustainable,and eco-friendly 2-methyltetrahydrofuran(2-MeTHF)as sol-vent.Compared with other reactions of electron-deficient olefin dipolarophiles with nitrones,different regioselective cycloaddition products were observed in this work.This 1,3-dipolar cycloaddition reaction gives a series of isoxazolidinyl nucleosides in good to excellent yields with promising applications in biochemistry and medicinal chemistry.

关 键 词：HETEROCYCLE NUCLEOSIDE CATALYST-FREE ANNULATION Regioselectivity Synthetic methods Cycloaddition 

分 类 号：O62[理学—有机化学]