10.1002/ejoc.200300795
The research focuses on the development of efficient conditions for the addition of acid enediolates to epoxides, offering an alternative to the traditional use of aluminum enolates. The study introduces a method that employs a sub-stoichiometric amount of amine for dianion generation and the activation of epoxides with lithium chloride (LiCl). The reactants used in the experiments include various epoxides and phenylacetic acid, which are subjected to nucleophilic addition reactions under these new conditions. The experiments are designed to optimize factors such as the amount and nature of the lithium amide used as a base, temperature, and reaction time. Analyses utilized to evaluate the outcomes encompass techniques like infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. The results indicated improved yields and selectivity in the formation of ?-lactones or hydroxy acids, which could be further converted to ?-lactones upon refluxing in toluene. The study also explored the impact of different Lewis acids and additives on the reaction's diastereoselectivity and regioselectivity, with LiCl showing the most promising results, particularly when used in inverse addition.
10.1016/S0960-894X(02)01003-X
The study focuses on the structure-activity relationships of novel anti-malarial agents, specifically N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2furyl]acrylic acid amides. The researchers developed a lead compound, benzophenone 4g, which was modified by replacing the tolylacetyl residue at the 2-amino group with various acyl residues to determine their influence on anti-malarial activity. The chemicals used included 2-amino-5-nitrobenzophenone, acid chlorides for acylation, SnCl2?2H2O for reduction, and 3-[5-(4-nitrophenyl)-2-furyl]acrylic acid chloride for further acylation. The purpose of these chemicals was to synthesize and test a series of compounds to identify the optimal acyl residue structure for high anti-malarial activity, with the aim of overcoming drug resistance in Plasmodium falciparum, the causative agent of malaria. The study found that a phenylacetic acid substructure substituted in its para-position with methyl or similar-sized substituents was essential for high activity, with the trifluoromethyl-substituted derivative showing the most potent activity.
10.1016/j.tetlet.2014.11.015
The study presents a novel synthetic method for the production of benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives, which are significant in synthetic strategies due to their presence in biologically active compounds. The synthesis involves the use of ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting materials, respectively. Key intermediates in this process are compounds bearing the oxazole-4-carboxylic acid methylester moiety. The study details the synthesis process, which includes the use of reagents such as HBr/HAc for the production of benzofuran-2-yl-methanamines and HCl for the synthesis of indol-2-yl-methanamines after the reduction of the nitro-group. The method is effective with electron-donating substituents but has limitations with electron-withdrawing substituents. The study also discusses the availability and preparation of the starting phenylacetic acids and explores the synthetic procedure's applicability to a variety of substituted phenylacetic acids, demonstrating its potential as a general synthetic method for these compounds.
10.1002/ardp.19883210506
The research focuses on mass spectrometric investigations of derivatives of phenylacetic acid, specifically examining the loss of ortho-substituents from ionized phenylacetamides. The purpose of this study was to explore the mass spectrometry (MS) behavior of ortho-substituted phenylacetamides, particularly the loss of substituents such as chlorine, bromine, and nitro groups, which result in strong (M-X)+ signals in their 70 and 12 eV mass spectra. The research concluded that the loss of ortho-substituents is position-specific, with additional methoxy substitution facilitating the loss of the ortho-nitro group. The study also discussed the MI- and CAD-spectra of the (M-X')+-ions and proposed that a special ortho-effect might be at play, where the ortho-substituent is replaced by an intramolecular attack of the amide group. Various phenylacetamides, including 2a-h, 3a-g, 4a, b, 5a, b, and others, were synthesized from corresponding phenylacetic acids using SOCl2 and then with aqueous ammonia or dimethylamine. The chemicals used in the process encompassed a range of phenylacetamides with different substituents, such as H, CH3, F, Cl, Br, NO2, and OCH3, among others, to investigate their specific mass spectrometry patterns and fragmentation behaviors.
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