10.1016/j.tetlet.2011.01.003
The study develops an efficient and environmentally friendly method for the N-arylation of amides using aryl halides, catalyzed by ligand-free copper(I) oxide (Cu2O) in water. This method provides a practical approach to synthesizing N-arylated amides, which are valuable in pharmaceuticals and materials science. The research focuses on optimizing reaction conditions, including the choice of copper catalyst, base, and phase-transfer catalyst, to achieve good to excellent yields of the desired N-arylated products. The method proves effective for a variety of amides and aryl iodides, making it a versatile tool for organic synthesis.
10.1016/j.tet.2018.03.054
The research focuses on the development of novel organocatalysts by combining prolinamides with 2-pyrrolidinone for the asymmetric aldol reaction, a key C-C bond forming reaction in asymmetric catalysis. The experiments involved the synthesis of a series of organocatalysts through peptide coupling reactions and tested their efficiency in both organic and aqueous media. The reactants included various prolinamide derivatives, 2-pyrrolidinone derivatives, and other reagents used in the coupling process. The analyses used to evaluate the catalysts' performance included determining yields by 1H NMR, diastereomeric ratios (dr) by 1H NMR spectroscopy, and enantioselectivities (ee) by chiral HPLC. The study also explored the substrate scope and the potential for catalyst reuse, proposing a transition-state model to explain the stereoselectivity observed in the reactions.
10.1039/b209123b
The research focuses on the development of an enantio- and diastereo-selective approach to substituted pyrrolidinones using manganese(III) acetate-mediated alkylation of β-keto esters and β-keto amides. The purpose of this study was to efficiently construct quaternary carbon centers through intermolecular radical addition reactions, utilizing β-keto esters and amides with enol ethers and manganese(III) acetate in the presence of copper(II) acetate. The conclusions drawn from the research indicate that manganese(III) acetate can be effectively used to introduce functionalized side-chains at the α-position of α-substituted β-keto esters and amides, including pyrrolidinones, offering a favorable alternative to traditional base-mediated alkylation methods.
10.1016/0957-4166(95)00423-8
The research focuses on the synthesis of diastereomerically pure pyrrolidin-2-ones and their subsequent conversion into both (S)- and (R)-3-pyrrolidineacetic acids. The purpose of this study is to develop an efficient synthetic route for these non-proteinogenic amino acids, which have potential applications as inhibitors of GABA uptake in neurological disorders such as Parkinson's disease and epilepsy. The researchers achieved this by employing an intramolecular Michael reaction, starting from amides derived from (S)-phenylethylamine. The study successfully demonstrated the synthesis of the target compounds with good yields and high diastereomeric ratios, highlighting the potential of this method for preparing enantiomerically pure 3-pyrrolidineacetic acids.
10.1007/s10593-008-0093-6
The study focused on the reaction of phenyl glycidyl ether with various heterocyclic compounds to synthesize new compounds with potential biological activity. The chemicals used included 5,5-dimethylhydantoin, morpholine, benzotriazole, benzimidazole, pyrrolidone, phthalimide, and 8-hydroxyquinoline. These heterocyclic compounds served as reactants to form N-(2-hydroxy-3-phenoxypropyl) derivatives, which are of interest due to their potential to contain pharmacophoric fragments that could lead to the discovery of new biologically active substances. The purpose of the study was to develop a one-stage method for synthesizing these derivatives, which could be applied in preparative chemistry and contribute to the development of new drugs.
10.1039/d0nj04548a
The research explores an efficient and environmentally friendly method for synthesizing pharmaceutically important butyrolactam derivatives through the amination and carbonation of N-acyliminium ions. The study aims to develop a simple, chromatography-free, and efficient iron-catalyzed process for the functionalization of butyrolactam derivatives under mild conditions. Key chemicals used include butyrolactam derivatives as electrophilic precursors, various N-/C-nucleophiles such as sulfonamides, amines, amides, indoles, and 1,3-dicarbonyl compounds, and FeCl3·6H2O as the optimal catalyst. The reaction conditions were optimized to achieve high yields of the desired products, with alcohol being the only by-product. The study concluded that this method provides an inexpensive and practical approach to synthesizing gem-diamino derivatives and other butyrolactam derivatives, with a wide substrate scope and synthetic simplicity. The use of N-acyliminium ions as N-alkylating agents complements existing amination strategies and advances the field of catalytic N-acyliminium ion chemistry.
