The Chemistry of Ynamide and its Application in Organic Synthesis
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2020Keyword
YnamideYndiamide
Thioenamide
Haloenamide
Keteniminium
Witulski rearrangment
Ullmann coupling
Dipolar cycloaddition
α-ketoimide
Polycyclic alkaloids
Peer-Reviewed
YesOpen Access status
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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.Version
Accepted manuscriptCitation
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 Version of Record
https://doi.org/10.2174/9789811405082120130004Type
Book chapterae974a485f413a2113503eed53cd6c53
https://doi.org/10.2174/9789811405082120130004