332183-35-4

Upstream product

• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 332183-39-8 (4R,5S)-1,5-Dimethyl-4-phenyl-3-((E)-styryl)-imidazolidin-2-one 

Downstream Products

• 1092383-19-1 1-((4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl)-2-phenylethane-1,2-dione 

Relevant academic research and scientific papers

Copper-catalyzed alkynylation of amides with potassium alkynyltrifluoroborates: A room-temperature, base-free synthesis of ynamides

(Figure Presented) An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.

Highly regio- and stereocontrolled synthesis of β-substituted α-tributylstannyl enamides

The regio- and stereocontrolled synthesis of β-substituted α-stannyl enamides is reported starting from internal ynamides. The synthesis of new ynamides as well as bis-ynamides is also described. Finally first examples of successful cross-coupling to afford α/β-disubstituted enamides are also reported.

Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides

(Equation presented) A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO4·5H2O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.

Copper-Mediated N-Alkynylation of Carbamates, Ureas, and Sulfonamides. A General Method for the Synthesis of Ynamides

(Matrix Presented) A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.

Efficient preparations of novel ynamides and allenamides

Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.