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Synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide

Research paper by Zhan-guo Chen, Wei Xia, Hua Wen, Dan Wang, Ya-nan Li, Jun-li Hu

Indexed on: 11 Jul '13Published on: 11 Jul '13Published in: Chemical Research in Chinese Universities



Abstract

An efficient method for the one-pot synthesis of 2-oxazolines from ethyl α-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 α-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition-cyclization pathway was proposed.