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

doi:10.6023/cjoc201210034

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 1088-1095.DOI: 10.6023/cjoc201210034 Previous Articles Next Articles

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一种有效合成3-芳基-4-氟烷基-2-噁唑烷酮的方法

杨波^a, 赵敏^a, 方向^a, 杨雪艳^a, 吴范宏^a,b

a 华东理工大学化学与分子工程学院上海 200237;
b 上海应用技术学院化学与环境工程学院上海 201418

收稿日期:2012-10-18 修回日期:2013-01-21 发布日期:2013-01-25
通讯作者: 杨雪艳,yxy@ecust.edu.cn,吴范宏,wfh@ecust.edu.cn E-mail:yxy@ecust.edu.cn;wfh@ecust.edu.cn
基金资助:
国家自然科学基金(Nos. 20972050, 21172148).

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

Yang Bo^a, Zhao Min^a, Fang Xiang^a, Yang Xueyan^a, Wu Fanhong^a,b

a School of Chemistry and Molecular Enineering, School of Chemistry and Molecular Enineering, East China University of Science and Technology, Shanghai 200237;
b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235

Received:2012-10-18 Revised:2013-01-21 Published:2013-01-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972050, 21172148).

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.

Key words: oxazolidin-2-ones, fluorinated alkyl, synthesis, N-cyclizaion

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Yang Bo, Zhao Min, Fang Xiang, Yang Xueyan, Wu Fanhong. A Convenient Synthesis of 3-Aryl-4-fluoroalkyl-2-oxazolidinone[J]. Chin. J. Org. Chem., 2013, 33(05): 1088-1095.

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一种有效合成3-芳基-4-氟烷基-2-噁唑烷酮的方法

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

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