Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 999-1005.DOI: 10.6023/cjoc201311020 Previous Articles     Next Articles



范学森a, 李培源a, 李坤a,b, 张新迎a, 赵婉a   

  1. a 河南师范大学化学化工学院 新乡 453007;
    b 周口师范学院化学系 周口 466000
  • 收稿日期:2013-11-13 修回日期:2013-12-28 发布日期:2014-01-22
  • 通讯作者: 范学森
  • 基金资助:

    国家自然科学基金(Nos. 21172057,21272058)、教育部长江学者和创新团队发展计划(No. IRT 1061)、教育部博士点基金(No. 20114104110005)及国家大学生创新实验(No. 20120055)资助项目.

Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides

Fan Xuesena, Li Peiyuana, Li Kuna,b, Zhang Xinyinga, Zhao Wana   

  1. a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007;
    b Department of Chemistry, Zhoukou Normal University, Zhoukou 466000
  • Received:2013-11-13 Revised:2013-12-28 Published:2014-01-22
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21172057, 21272058), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) (No. IRT 1061), and the Research Fund for the Doctoral Program of Higher Education (RFDP) (No. 20114104110005).

6-Bromofuro[2,3-d]pyrimidine bicyclic nucleosides are the key intermediates for the preparation of novel furo[2,3-d]pyrimidine bicyclic nucleoside derivatives with remarkable antiviral potency. The literature protocol for their synthesis involves a multi-step procedure and palladium catalyst. In this paper, an economical and practical method for their preparation is developed via condensation of the easily obtainable 5-formyl pyrimidine nucleosides with carbon tetrabromide and subsequent cyclization promoted by copper iodide.

Key words: 6-bromofuro[2,3-d]pyrimidine bicyclic nucleosides, gem-dibromoalkenes, copper iodide