1353674-40-4

Upstream product

• 65680-20-8 phenylpropionic acid thioamide 
• 685-87-0 Diethyl 2-bromomalonate 
• 105-53-3 diethyl malonate 
• 102-93-2 3-phenylpropionamide 
• 5256-74-6 1,3-diethyl 2-diazopropanedioate 

Relevant academic research and scientific papers

A copper(I)-complexed magnetic nanoparticle catalyst for enaminone synthesis

The synthesis of a copper(I)-complexed magnetic nanoparticle catalyst is described. The catalyst was characterized using Fourier transform infrared spectroscopy (FT–IR), energy-dispersive X-ray spectroscopy (XPS), atomic absrobtion spectroscopy (AA), thermogravimetric analysis (TGA), vibrating sample magnetometery (VSM), X-ray photoelectron spectroscopy (XPS), scanning electron miscroscopy (SEM) and transmission electron microscopy (TEM). The catalyst coupled thioamides and diazocarbonyl compounds to produce diverse enaminones. The catalyst reduced the reaction times and temperature and provided enaminones in high yields and selectivity. Moreover, the catalyst can be separated by a magnet and recycled.

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

The development of operationally simple and cost-effective methods for C[sbnd]C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, α-diazoketosulfones and α-diazomonoketones.

Enaminones via ruthenium-catalyzed coupling of thioamides and α-diazocarbonyl compounds

Enaminones can be prepared via the Rh2(OAc)4- catalyzed coupling of α-diazocarbonyl compounds with thioamides. However, rhodium is the most expensive and least abundant among the dominant precious metals used for catalysis. Furthermore, a very limited substrate scope is known for the intermolecular rhodium catalyzed coupling reaction. Therefore, there is a need to find a more economical catalyst substitute with a broad substrate scope. In this paper, we describe the use of Ru(II) catalysts for the synthesis of enaminones. The reaction can be performed efficiently with the Grubbs first-generation catalyst or [(Ph)3P]3RuCl2 in a sealed tube. Both catalysts are much less expensive than Rh 2(OAc)4. Secondary and tertiary thioamides, when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, and α-diazomonoketones give enaminones. Primary thioamides give thiazole derivatives when reacted with α-diazomonoketones. However, with other diazo compounds, primary thioamides also give enaminones. All enaminones are obtained in good yields and with good diastereoselectivity. Accordingly, the method described in this paper is an efficient and economical alternative to the Rh2(OAc)4-catalyzed coupling process.

Acceleration of the Eschenmoser coupling reaction by sonication: Efficient synthesis of enaminones

Enaminones are commonly prepared by the Eschenmoser coupling reaction. The duration of the reaction is often long. Here, we describe how sonication can accelerate this reaction. The reaction conditions provide an efficient method for the coupling of prima

Ruthenium catalyzed synthesis of enaminones

The Grubbs first-generation catalyst has been found to be an effective catalyst for the synthesis of enaminones by coupling thioamides with α-diazodicarbonyl compounds. The reaction is successful in converting primary, secondary, and tertiary thioamides into their corresponding enaminones. The reaction is also suitable for the synthesis of chiral enaminones.