一种有效合成5-氟烷基噁唑啉的方法  

A Convenient Synthesis of 5-Fluoroalkyloxazoline

作　　者：杨波[1] 方向[1] 杨雪艳[1] 吴范宏[2] 

机构地区：[1]华东理工大学化学与分子工程学院,上海200237 [2]上海应用技术学院化学与环境工程学院,上海201418

出　　处：《有机化学》2013年第8期1782-1790,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.20972050;21172148)资助项目~~

摘　　要：报道了一种有效地合成5-氟烷基噁唑啉的方法.异氰酸酯与烯丙基胺在二氯甲烷中室温反应得到1-烯丙基-3-芳基脲.1-烯丙基-3-芳基脲与氟烷基碘在乙腈和水的混合液中由连二亚硫酸钠引发在室温下发生自由基加成反应得到氟烷基化的加成产物.加成产物在水或N,N-二甲基甲酰胺(DMF)中加热回流反应得到5-氟烷基噁唑啉.同时我们也可以通过由偶氮二异丁腈(AIBN)引发的1-烯丙基-3-芳基脲的加成环合反应得到5-氟烷基噁唑啉.An efficient and convenient protocol for the synthesis of 5-fluoroalkyl-2-oxazoline is described. The 1-allyl-3-arylurea was synthesized by the reaction of isocyanate with ally1 amine in methylene chloride at room temperature. The reaction of 1-allyl-3-arylurea with fluoroalky iodide initiated by sodium dithionite in aqueous acetonitrile resulted in adducts that undergoes a cyclization in water or DMF to form 5-fluoroalkyloxazoline with moderate yields. It was also found that the products can be more efficiently formed via an AIBN-initiated, one-pot addition-cyclization sequence from 1-allyl-3-arylurea with fluoroalkyl iodide.

关 键 词：噁唑啉 氟烷基化 O-环合 自由基反应 

分 类 号：O626[理学—有机化学]