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The Chemistry of Ynamide and its Application in Organic Synthesis

Siyu, Y.
; 
Publication Date
2020
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Keywords
Ynamide, Yndiamide, Thioenamide, Haloenamide, Keteniminium, Witulski rearrangment, Ullmann coupling, Dipolar cycloaddition, α-ketoimide, Polycyclic alkaloids
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Peer-Reviewed
Yes
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openAccess
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Life Sciences Publications
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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.
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Link to Version of Record
https://doi.org/10.2174/9789811405082120130004
Type
Book chapter
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