Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide  

作　　者：CHEN Zhan-guo XIA Wei WEN Hua WANG Dan LI Ya-nan HU Jun-li 

机构地区：[1]Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China

出　　处：《Chemical Research in Chinese Universities》2013年第4期699-705,共7页高等学校化学研究（英文版）

基　　金：Supported by the National Natural Science Foundation of China（Nos.20572066, 20906059） and the Natural Science Founda- tion of Shaanxi Province of China（No .2009JM2011）.

摘　　要：An efficient method for the one-pot synthesis of 2-oxazolines from ethyl a-cyanocinnamate derivatives with acetamide and N-bromosuccinimide（NBS） in the presence of K3PO4 was developed. The reaction was performed smoothly and cleanly to give 2-oxazolines in good to excellent yields（up to 95%） in acetone at room temperature. Thirteen examples were investigated and the results indicated that a large range of a-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition- cyclization pathway was proposed.An efficient method for the one-pot synthesis of 2-oxazolines from ethyl a-cyanocinnamate derivatives with acetamide and N-bromosuccinimide（NBS） in the presence of K3PO4 was developed. The reaction was performed smoothly and cleanly to give 2-oxazolines in good to excellent yields（up to 95%） in acetone at room temperature. Thirteen examples were investigated and the results indicated that a large range of a-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition- cyclization pathway was proposed.

关 键 词：One-pot synthesis OXAZOLINE ACETAMIDE N-Bromosuccinimide（NBS） Regioselectivity Nucleophilic ad-dition-cyclization 

分 类 号：TQ522.6[化学工程—煤化学工程] TQ252