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Formation of Enehydrazine Intermediates through Coupling of Phenylhydrazines with Vinyl Halides: Entry into the Fischer Indole Synthesis

Authors

  • Fuxu Zhan,

    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • Prof. Guangxin Liang

    Corresponding author
    1. State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
    • State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071 (China)
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  • We thank the State Key Laboratory of Elemento-organic Chemistry in China, the National Natural Science Foundation of China (Grant Nos. 20902049, 21172117, 21032003, 21121002), the Tianjin Natural Science Foundation (Grant No. 12JCYBJC26400) and the “111” project (B06005) of the Ministry of Education of China for financial support.

Abstract

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Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine.

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