Recent Advances in the Synthesis of Ynamides

Abstract

Ynamides are a class of special ynamines bearing an electron-withdrawing group on the nitrogen atom. The electron-withdrawing group endows ynamides an optimal balance between the stability and activity, and thus enabling ynamides to be versatile synthons widely used in organic synthetic chemistry. The ynamide chemistry has witnessed a rapid development over the past two decades. As a consequence, its synthetic methods have attracted widespread attention. In this context, the recent advances in the synthesis of ynamides are reviewed herein. According to the structure of the main starting materials, the contents are classified as the synthesis with haloenamides, alkynes or its derivatives, and dihalo-substituted alkenes. The representative mechanisms are also discussed.

Thiuram Disulfide Mediated Cu-Catalyzed Amidation of Terminal Alkynes: An Efficient Synthesis of Alkynyl Amides

“…They also serve as important synthetic building blocks in the field of organic synthesis . The common route for the synthesis of alkynyl amides involves the amidation reaction of alkynyl halides, alkynyl carboxylic acids, and alkynyl carboxaldehyde . However, amidation of terminal alkynes avoids the prefunctionalization of the C­(sp)–H bond; hence, it is synthetically more attractive.…”

Copper-Catalyzed C(sp)–H Bond Hydrazidation

“…Ynamides are versatile and useful synthetic building blocks and have attracted a great deal of attention from scientists over the past two decades . One of the subgroups, ynehydrazides, comprising a hydrazide motif link on an alkynyl through a C­(sp)–N bond (Scheme A), has been developed much less.…”