Advances in Organic Synthesis

Advances in Organic Synthesis

Volume: 13

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. The series presents comprehensive reviews written by eminent ...
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The Chemistry of Ynamide and Its Application in Organic Synthesis

Pp. 52-170 (119)

DOI: 10.2174/9789811405082120130004

Author(s): Siyu Ye, Na Wu

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.

Keywords:

Dipolar Cycloaddition, Haloenamide, Keteniminium, Polycyclic Alkaloids, Thioenamide, Ullmann Coupling, Witulski Rearrangment, α- Ketoimide, Ynamide, Yndiamide.