摘要
以9-苄基嘌呤和碘代丁二酰亚胺(NIS)为原料,研究开发了8-碘-9-苄基嘌呤合成的新方法.较佳反应条件为:反应溶剂THF,反应温度70 ℃,n(9-苄基嘌呤)∶n(NIS)＝1∶2.5,反应时间48 h.在此条件下,产品收率达87%以上.另外,以(Ph3P)2PdCl2 为催化剂,对8-碘-9-苄基嘌呤与有机基锡试剂RSnBu3之间的Stille偶合反应进行了研究.得到较佳反应条件为:反应温度80～100 ℃,n(8-碘-9-苄基嘌呤)∶n(RSnBu3)∶n((Ph3P)2PdCl2)= 1.0∶1.2∶0.05,反应时间24 h. 在上述条件下,产品收率为91%(R＝乙烯基)、 86%(R＝2-噻吩基)、90%(R＝2-呋喃基)、80%(R＝苯乙炔基)和42%(R＝苯基).采用1H-NMR、13C-NMR、MS、碳氢相关谱(HETCOR)和远程碳氢相关谱(Long Range HETCOR)等分析手段对所得产物结构进行了表征,证明其结构正确,并对两步反应的机理进行了探讨.
Iodo-9-benzylpurine was synthesized by using 9-benzylpurine and N-iodosuccinimide(NIS) as raw materials. Under the optimum reaction conditions of reaction temperature 70 ℃, n(9-benzylpurine):n(NIS) =1.0∶2.5 and reaction time 48 h, the yield of product was over 87%. Moreover, the Stille coupling reaction between 8-iodo-9-benzylpurine and RSnBu 3(R=vinyl, 2-thienyl, 2-furyl, phenylethynyl and phenyl) was studied using (Ph 3P) 2PdCl 2 as catalyst. Under the optimum reaction conditions of reaction temperature 80~100 ℃, n(8-iodo-9-benzylpurine)∶n(RSnBu 3)∶n [(Ph 3P) 2PdCl 2] = 1.0∶1.2∶0.05 and reaction time 24 h, the yield of product was 42%~91%.The product was characterized by 1H-NMR, 13C-NMR, MS, HETCOR and Long Range HETCOR and the reaction mechanism was discussed.
出处
《青岛科技大学学报（自然科学版）》
CAS
2005年第2期95-100,共6页
Journal of Qingdao University of Science and Technology:Natural Science Edition
基金
山东省优秀中青年科学家科研奖励基金资助(02BS107)
