Refernces
10.1016/j.tet.2005.05.055
The study focuses on the synthesis and evaluation of galanthamine analogs, specifically 6H-benzofuro[3a,3,2-e,f][1]benzazepine and 6H-benzofuro[3a,3,2-e,f][3]benzazepine, which are derivatives of the Amarylidaceae alkaloid galanthamine. Galanthamine is known for its cholinesterase inhibitory properties and is used in the treatment of neuromuscular diseases and Alzheimer's dementia. The purpose of the study was to alter the position of the nitrogen within the azepine ring of galanthamine to create analogs that might have similar or improved therapeutic effects. The synthesis involved a variety of chemicals, including p-hydroxyphenylpropionic acid, benzyl chloride, thionyl chloride, and various other reagents and solvents, which were used to perform esterification, benzylation, saponification, formylation, bromination, and reduction reactions, among others. These chemicals served to construct the complex molecular structures of the analogs, with the ultimate goal of understanding how changes in the molecular structure affect the reactivity and potential therapeutic applications of these compounds.
10.1021/jo00317a030
The study investigates the synthesis and properties of substituted 2,6-dioxabicyclo[3.1.1]heptanes, specifically focusing on the compounds 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-mannopyranose and 1,3-anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose. These compounds are synthesized through a series of reactions involving various reagents such as dibutyltin oxide, allyl bromide, benzyl chloride, and p-bromobenzyl bromide. The synthesis process includes steps like acetylation, benzylation, and ring closure using strong bases like sodium hydride (NaH) and potassium tert-butoxide (t-BuOK). The study aims to produce these anhydro sugars as precursors for the synthesis of 1,3-mannopyranans by ring-opening polymerizations, which are of interest for their potential applications in immunological and biochemical investigations. The compounds' structures are confirmed through mass spectrometry, 1H NMR, and 13C NMR spectroscopy, and their stability and purity are assessed through various analytical techniques.
10.1016/S0040-4039(00)96022-2
The study investigates the thermal decomposition of 3-benzyloxy-3-chlorodiazirine in acetonitrile at 25°C to produce benzyloxychlorocarbene, which further fragments to form the benzyl cation. The researchers conducted a detailed analysis of the reaction, examining the effects of different solvents and solvent conditions on the fragmentation process. They found that the reaction proceeded cleanly in acetonitrile, with only minor solvent effects on the rate constant. The study also included an Arrhenius study to determine the energy of activation and a Hammett study to understand the reaction's sensitivity to substituent effects. The researchers proposed that the thermal fragmentation of benzyloxychlorocarbene yields intermediates such as ion pairs and suggested that the geometry of the diazirine prior to decomposition may influence the distribution of these ion pairs. Additionally, they explored the photolytic decomposition of the compound and observed the formation of benzyl radical, although they concluded that this was not the principal pathway for the fragmentation of the carbene. The study was supported by the National Science Foundation and contributed to the understanding of carbene chemistry and the formation of carbocations.
10.1002/jhet.4167
The study focuses on the synthesis, characterization, and evaluation of novel 1,5-benzodiazepine derivatives (compounds 2-7) for their potential applications in corrosion inhibition and antibacterial activities. The chemicals used in the study include 1-ethyl-4-phenyl-1,5-benzodiazepine-2-thione, phosphorus pentasulfide, hydrazine hydrate, carbon disulfide, and various alkylating agents such as propargyl bromide, benzyl chloride, and ethyl bromoacetate. These chemicals served the purpose of synthesizing the target benzodiazepine derivatives through a series of reactions including sulfurization, condensation, and alkylation. The synthesized compounds were then characterized using spectroscopic techniques and single-crystal X-ray crystallography. The study aimed to determine the molecular and crystal structures of these compounds, analyze their intermolecular interactions through Hirshfeld surface analysis, and evaluate their potential as corrosion inhibitors for aluminum, copper, and iron in acidic media using Monte Carlo simulations. Additionally, the antibacterial activity of these compounds against Gram-positive and Gram-negative bacteria was assessed, with the results indicating their potential as antibacterial agents.
10.1002/chem.200400733
The research focuses on the practical synthesis of (+)-biotin from l-cysteine, a significant endeavor due to biotin's crucial role in human nutrition and animal health. The study aims to address the inefficiencies of the existing Goldberg and Sternbach method, which involves over 14 steps, utilizes toxic reagents, and requires impractical diastereomeric or enzymatic resolution. The researchers developed a novel synthetic approach that eliminates the need for bulky protecting groups and reduces the protection-deprotection sequence steps. This method involves the formation of contiguous stereogenic centers through a highly diastereoselective Strecker reaction, a novel ring transformation and deblocking by S,N-carbonyl migration, and the introduction of the carbon chain at C-4 by the Fukuyama coupling reaction. Key chemicals used in the process include l-cysteine, phenyl chloroformate, benzyl bromide, benzyl chloride, sodium bisulfite, sodium cyanide, and various catalysts and reagents for the reactions involved. The conclusions of the research highlight the successful development of a more efficient synthetic method for (+)-biotin, achieved in 10 steps and with an overall yield of 34% from l-cysteine, offering a high yield, ease of operation, and mild reaction conditions.
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