有机化学 ›› 2014, Vol. 34 ›› Issue (5): 999-1005.DOI: 10.6023/cjoc201311020 上一篇    下一篇

研究简报

6-溴代呋喃[2,3-d]嘧啶双环核苷的合成新方法研究

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 出版日期:2014-05-25 发布日期:2014-01-22
  • 通讯作者: 范学森 E-mail:xuesen.fan@htu.cn
  • 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 Online:2014-05-25 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-溴代呋喃[2,3-d]嘧啶双环核苷是合成具有显著抗病毒活性的呋喃并嘧啶双环核苷衍生物的重要中间体. 该类化合物的文献制备方法合成步骤多,并需使用钯配合物作催化剂. 以易得的5-甲酰基嘧啶核苷为原料,先经与四溴化碳缩合得5-(2,2-二溴乙烯基)嘧啶核苷类似物,然后在碘化亚铜催化下发生环化反应生成目标产物,不仅缩短了合成路线,而且避免了贵金属试剂的使用,是一种经济实用的新方法.

关键词: 6-溴代呋喃[2,3-d]嘧啶双环核苷, 偕二溴烯烃, 碘化亚铜

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