73964-79-1Relevant articles and documents
Synthesis of pyrrolidones and quinolines from the known biomass feedstock levulinic acid and amines
Ortiz-Cervantes, Carmen,Flores-Alamo, Marcos,García, Juventino J.
supporting information, p. 766 - 771 (2016/02/05)
The catalytic conversion of biomass-derived compounds into value-added products such as food additives, agrochemical components, and pharmaceutical formulations, is a promising and cost effective synthetic strategy. Here, we describe the synthesis of a variety of N-(alkyl, aryl)-5-methyl-2-pyrrolidones through the reductive amination of levulinic acid using formic acid as the hydrogen source. This system is catalyzed by 3.8 nm ruthenium nanoparticles that were prepared by thermal decomposition of [Ru3(CO)12] in solvent-free conditions. When the reactions were carried out without the catalyst, the pyrrolidones were obtained with low yield and poor selectivity. In addition, the reaction between levulinic acid and 2-ethynylaniline produced 2-(2,4-dimethylquinolin-3-yl) acetic acid (8) in mild and metal-free conditions with good yield. Furthermore, the synthesis of substituted quinolines was achieved through a condensation reaction between levulinic acid and different 2-alkynylanilines promoted by p-toluenesulfonic acid, this method is highlighted as a novel procedure for the preparation of quinolines.
Formation of γ-keto esters from β-keto esters: Methyl 5,5-dimethyl-4-oxohexanoate: [Hexanoic acid, 5,5-dimethyl-4-oxo-, methyl ester]
Ronsheim, Matthew D.,Hilgenkamp, Ramona K.,Zercher, Charles K.,Denmark, Scott E.,Beutner, Gregory L.
, p. 146 - 146 (2017/09/08)
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Zinc carbenoid-mediated chain extension of β-keto amides
Hilgenkamp, Ramona,Zercher, Charles K
, p. 8793 - 8800 (2007/10/03)
The reaction of β-keto amides with ethyl(iodomethyl)zinc provides access to a wide variety of γ-keto amides, including primary, secondary, and tertiary amides. Although the reaction of α-substituted β-keto amides are in many cases unsatisfactory, the method can be applied to a broad spectrum of substrates that possess imide and olefinic functionality.
