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NaH-promoted one-pot synthesis of 5-amidoimidazoles from arylamines, carbon disulfide and isocyanides

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Abstract

A novel, convenient and efficient protocol to access functionalized 5-amidoimidazoles is developed via one-pot synthesis from readily available materials of arylamines, carbon disulfide and isocyanides. The transformation was realized at room temperature and provided 5-amidoimidazoles in moderate to good yields in the presence of NaH. In addition, control experiments indicated that the process might be achieved via the base-induced cyclization of activated methylene isocyanides with N,N-disubstituted thioureas that produced from the reaction of amines and carbon disulfide.

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Acknowledgements

The work was financially supported by the National Innovation and Entrepreneurship Training Program for college students (No. 202010349031) and Natural Science Foundation for colleges and universities in Anhui Province (No. YJS20210138).

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  1. Jie Luo, Yichan Zhang, Qiuxia Yan, Guo Yang: Contributed equally to this work

Authors and Affiliations

  1. College of Yuanpei, College of Chemistry and Chemical Engineering, College of Life Sciences, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, 312000, Zhejiang, People’s Republic of China

    Jie Luo, Qiuxia Yan, Guo Yang, Yaohong Zhang & Hai Wang

  2. Department of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, 224051, Jiangsu, People’s Republic of China

    Yichan Zhang

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  1. Jie Luo
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Luo, J., Zhang, Y., Yan, Q. et al. NaH-promoted one-pot synthesis of 5-amidoimidazoles from arylamines, carbon disulfide and isocyanides. Mol Divers 27, 135–143 (2023). https://doi.org/10.1007/s11030-022-10413-9

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