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A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

Authors

  • Dr. Guolin Cheng,

    1. Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)
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  • Xiaobao Zeng,

    1. Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)
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  • Jinhai Shen,

    1. Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)
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  • Xuesong Wang,

    1. Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)
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  • Prof. Xiuling Cui

    Corresponding author
    1. Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)
    2. Department of Chemistry, Zhengzhou University, Zhengzhou 450052 (P. R. China)
    • Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Xiamen Marine and Gene Drugs, Institutes of Molecular Medicine and School of Biomedical Sciences, Huaqiao University, Xiamen 361021 (P. R. China)===

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  • This work was supported by the National Natural Science Foundation of China (21202048), Program for Minjiang Scholar (10BS216), Science Research Item of Science and Technology of Xiamen City (3502z201014), and the Natural Science Foundation of Fujian Province, China (2013J01050).

Abstract

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About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).

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