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A Variation of the Fischer Indolization Involving Condensation of Quinone Monoketals and Aliphatic Hydrazines

Authors

  • Dr. Jinzhu Zhang,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Zhiwei Yin,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Patrick Leonard,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Jing Wu,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Kate Sioson,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Che Liu,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Robert Lapo,

    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
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  • Prof. Dr. Shengping Zheng

    Corresponding author
    1. Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
    2. The Graduate Center, The City University of New York, 365 5th Avenue, New York, NY 10016 (USA)
    • Department of Chemistry and Biochemistry, Hunter College, 695 Park Avenue, New York, NY 10065 (USA)
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  • We are grateful to Professors Richard Franck, Randy Mootoo, Klaus Grohmann, and William Berkowitz for helpful discussions. We also thank Dr. Cliff Soll, Dr. Yashuhiro Itagaki, and Dr. Matthew Devany for with assistance mass spectrometry and NMR spectroscopy. Financial support from the Bertha and Louis Weinstein Research Grant, PSC-CUNY Award, and the President’s Fund for Faculty Advancement Award of Hunter College is gratefully acknowledged.

Abstract

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A new twist: A one-pot nitrous acid free, diazonium-free, and transition-metal-free variation of the Fischer indole synthesis has been developed. Condensation of quinone monoketals and aliphatic hydrazine hydrochlorides afforded indoles via intermediate alkylaryldiazenes. This method will complement the classical Fischer indole synthesis by providing indoles in two steps from widely available phenols under mild conditions.

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