| Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide |
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| 基金项目： | Supported by the National Natural Science Foundation of China(Nos.20572066, 20906059) and the Natural Science Foundation of Shaanxi Province of China(No.2009JM2011). |
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| 摘 要： |
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| 收稿时间： | 2012-10-31 |
Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide |
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| CHEN Zhan-guo , XIA Wei , WEN Hua , WANG Dan , LI Ya-nan , HU Jun-li. Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Acetamide and N-Bromosuccinimide[J]. Chemical Research in Chinese University, 2013, 29(4): 699-705. DOI: 10.1007/s40242-013-2420-4 |
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| Authors: | CHEN Zhan-guo XIA Wei WEN Hua WANG Dan LI Ya-nan HU Jun-li |
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| Affiliation: | Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China |
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| 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. |
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| Keywords: | One-pot synthesis Oxazoline Acetamide N-Bromosuccinimide(NBS) Regioselectivity Nucleophilic addition-cyclization |
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