A Convenient Synthesis of 3-Aryl-4-fluoroalkyl-2-oxazolidinone

作者:Yang Bo*; Zhao Min; Fang Xiang; Yang Xueyan; Wu Fanhong
来源:Chinese Journal of Organic Chemistry, 2013, 33(5): 1088-1095.
DOI:10.6023/cjoc201210034

摘要

An efficient and convenient protocol for the synthesis of 3-aryl-4-fluoroalkyl-2-oxazolidinones is described. The allyl arylcarbamates were obtained from the corresponding aromatic amine and chloroformate allyl ester in high yields. The reaction of allyl arylcarbamates with fluoroalkyl iodide initiated by sodium dithionite in aqueous acetonitrile afforded adducts, which underwent cyclization in the presence of sodium hydride to give corresponding 3-aryl-4-fluoroalkyl-2-oxazolidinone in middle yield. All reactions were carried out in room temperature without phosgene to obtain 3-aryl-4-fluoroalkyl-2-oxazolidinone. The advantages of this method are that the raw material is easy to get, the operation is simple, it is green and environmental-protection.