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    The Chemistry of Ynamide and its Application in Organic Synthesis

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    Publication date
    2020
    Author
    Siyu, Y.
    Wu, Na (Anna)
    Keyword
    Ynamide
    Yndiamide
    Thioenamide
    Haloenamide
    Keteniminium
    Witulski rearrangment
    Ullmann coupling
    Dipolar cycloaddition
    α-ketoimide
    Polycyclic alkaloids
    Peer-Reviewed
    Yes
    Open Access status
    Green
    
    Metadata
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    Abstract
    Ynamide, is an understudied but attractive class of alkynes, activated by the donating ability of the nitrogen adjacent to alkynes. With the nucleophilicity on β-carbon and the electrophilicity on α-carbon of ynamides, this review summarizes the syntheses of ynamides and miscellaneous reactions - oxidation, rearrangement, cyclization, and cycloaddition to construct complicated heterocyclic rings. The synthetic methodologies were further applied into natural products synthesis, e.g. marinoquinolines A and C, aplidiopsamine A, rigidin A, and 7-azaserotonin derivative.
    URI
    http://hdl.handle.net/10454/18435
    Version
    Accepted manuscript
    Citation
    Siyu Y and Wu N (2020) The Chemistry of Ynamide and its Application in Organic Synthesis. In: Rahman AU (Ed) Advances in Organic Synthesis. Volume 13. Singapore: Bentham Science Publishers.
    Link to publisher’s version
    https://doi.org/10.2174/9789811405082120130004
    Type
    Book chapter
    Collections
    Life Sciences Publications

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