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

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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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Authors and Affiliations

  1. Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. China

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

Authors
  1. Zhan-guo Chen
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  2. Wei Xia
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  3. Hua Wen
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  4. Dan Wang
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  5. Ya-nan Li
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  6. Jun-li Hu
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Corresponding author

Correspondence to Zhan-guo Chen.

Additional information

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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Chen, Zg., Xia, W., Wen, H. et al. Synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide. Chem. Res. Chin. Univ. 29, 699–705 (2013). https://doi.org/10.1007/s40242-013-2420-4

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  • DOI: https://doi.org/10.1007/s40242-013-2420-4

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