6-溴代呋喃[2,3-d]嘧啶双环核苷的合成新方法研究有机化学.pdfVIP

DOI: 10.6023/cjoc201311020 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 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 (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) 摘要 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 Novel and Efficient Synthesis of 6-Bromofuro[2,3-d]pyrimidine Bicyclic Nucleosides Fan, Xuesen*,a Li, Peiyuana Li, Kuna,b Zhang, Xinyinga Zhao, Wana a ( School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007 ) b ( Department of Chemistry, Zhoukou Normal University, Zhoukou 466000) Abstract 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 syn- thesis 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 prom