5-氟烷基-2-噁唑烷酮的快速合成  

Expeditious Synthesis of 5-Fluoroalkyl-Oxazolidin-2-Ones

作　　者：杨波[1] 方向[1] 赵敏[1] 吴晶晶[2] 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：《上海应用技术学院学报（自然科学版）》2013年第4期269-277,共9页Journal of Shanghai Institute of Technology: Natural Science

摘　　要：报道了一种用微波法方便有效地合成5．氟烷基-2-嗯唑烷酮的方法。以芳基胺为起始原料，通过与氯甲酸苄酯反应以57．8％～99．7％的高收率得到芳基氨基甲酸苄酯。芳基氨基甲酸苄酯在氢化钠存在下，与烯丙基溴反应以96．3％～99．9％的收率得到芳基烯丙基氨基甲酸酯。芳基烯丙基氨基甲酸酯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。加成产物在微波加热下发生分子内的O-环合反应，以67．7％～90．3％的收率得到5-氟烷基-2-嗯唑烷酮。An efficient and convenient approach for synthesizing 5-fluoroalkyl-3-aryl-oxazolidin-2-ones was described. The allyl （aryl or alkyl） carbamates were generated with high yields of 96.3% - 99.9% by using the arylamine as the starting material to make reaction with benzyl chloroformate. The reaction of allyl （aryl or alkyl） carbamates with fluoroalkyl iodide initiated by sodium dithionite in aqueous aceto- nitrile afforded the corresponding adducts which subsequently underwent an intramolecular O-cycliza- tion reaction assisted by microwave irradiation to generate 5-fluoroalkyl-3-aryl-oxazolidin-2-ones with high yields of 67.7 % - 90.3 %.

关 键 词：2-噁唑烷酮 氟烷基化 微波 O-环合 

分 类 号：O626[理学—有机化学]