Refernces
10.1002/adsc.202000618
The research focuses on the electrochemical synthesis of O-phthalimide oximes from α-azido styrenes via a radical sequence involving the generation, addition, and recombination of imide-N-oxyl and iminyl radicals, leading to the formation of C-O and N-O bonds. The study utilizes vinyl azides and N-hydroxyphthalimide as reactants and employs an electrochemical approach to induce the radical-initiated reaction, resulting in O-phthalimide oximes containing the challenging N-O-N fragment. Experiments involve the optimization of reaction conditions, such as solvent type, electrolyte, base, and current density, to achieve the highest yields of O-phthalimide oximes, which were analyzed using techniques like 1H NMR spectroscopy and column chromatography. The research also includes the use of radical scavengers, cyclic voltammetry, and EPR spectroscopy to confirm the radical nature of the process and to elucidate the reaction mechanism.
10.1016/j.bmcl.2009.03.130
The study focuses on the synthesis and biological activity of a low molecular weight non-peptidic mimic of the analgesic peptide x-conotoxin GVIA, which is a calcium channel (Cav2.2) blocker with potential applications in pain management. The researchers aimed to develop a compound with improved oral bioavailability and blood-brain barrier permeability by reducing its molecular weight. Key chemicals used in the study include 2-aminobenzothiazole, various acids, amines, and protecting groups like phthalimide and BOC. These chemicals were employed in the synthesis of several 'truncated' analogues of the lead compound 1b, which were designed to mimic specific amino acid residues of x-conotoxin GVIA. The purpose of these chemicals was to create a series of compounds with varying structures to evaluate their effectiveness in inhibiting N-type calcium channels, with the goal of identifying a lead compound that is both biologically active and more suitable for drug development due to its lower molecular weight and simplified synthesis process.
10.1002/anie.202009699
The study presents a unified strategy for synthesizing various arylsulfur(VI) fluorides, including Ar-SOF3 compounds, from commercially available aryl halides. The process involves a novel sulfenylation reaction using electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents to form Ar-S-Phth compounds, which are then selectively oxidized under mild conditions to produce distinct fluorinated sulfur(VI) compounds. The oxidation step can be modified to chemoselectively install 1, 3, or 4 fluorine atoms at the S(VI) center, yielding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl respectively. The study's purpose is to provide a convenient and efficient method for accessing these compounds, which are of interest due to their potential applications in organic synthesis and as electrophiles. The strategy also enables the introduction of the rare -SOF3 moiety into various (hetero)aryl groups and demonstrates the potential use of Ar-SOF3 as a precursor for synthesizing aryl sulfonimidoyl fluorides (Ar-SO(NR)F).
10.1002/ejic.200300617
The research presented focuses on the synthesis and study of aminomethyl and aminoacetyl complexes of palladium(II), platinum(II), iron(II), and rhenium(I) with N-phthaloyl as an amino protecting group. The study also delves into the mechanistic aspects of palladium-catalyzed amidocarbonylation, a process for forming a-amino acids from aldehydes, amides, and carbon monoxide. The researchers synthesized new complexes through oxidative addition reactions using various metal carbonyls and organic halides, yielding compounds such as [Re{C(O)CH2N-phthaloyl}(CO)5], [FeCp(CH2N-phthaloyl)(CO)2], [FeCp{C(O)CH2N-phthaloyl}(CO)2], trans-[PdBr(CH2N-phthaloyl)(PPh3)2], and trans-[Pd{C(O)CH2N-phthaloyl}(X)(PPh3)2], among others. They performed ligand exchange reactions to obtain bis(phosphane) complexes and cationic chelate complexes through halide abstraction. The structures of several compounds were confirmed via single-crystal X-ray analysis. To investigate the mechanism of the palladium-catalyzed amidocarbonylation, they utilized a model system consisting of phthalimide, formaldehyde, and carbon monoxide, which led to the formation of N-phthaloylglycine. The study employed various analytical techniques, including infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy, to characterize the synthesized complexes and monitor the reaction progress. The results provided insights into the elementary steps of the catalytic cycle and confirmed the proposed mechanism for the amidocarbonylation process.
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.
