Synonyms:MFCD00003536;Sodium azide (NaN3);NSC3072;HMS3871M13;BP-12548
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The research presents a stereoselective synthesis of (2S,3S)-sa?ngol and its natural (2S,3R)-isomer from 3,4,6-tri-O-benzyl glycals. The key step in the synthesis involves a one-pot reduction of an azide, saturation of double bonds, and debenzylation under catalytic hydrogenation. The synthesis route leverages carbohydrate-based chiral pool starting materials to construct both stereocenters with good overall yields of 21% and 36%, respectively. Reactants used include 3,4,6-tri-O-benzylated glycals, which undergo Perlin hydrolysis and acetylation to form trans-enals. These are then subjected to Wittig reaction to yield trans dienes, which are further converted to the final products through a series of reactions involving sodium methoxide, mesyl chloride, sodium azide, and catalytic hydrogenation with palladium on carbon. Analyses used to characterize the synthesized compounds include spectral data such as infrared (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS), which were found to be in good agreement with reported data of the natural materials.
The study presents a one-pot, two-step synthesis method for the creation of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives, which are important heterocyclic compounds with applications in pharmaceuticals and other industries. The process involves an N-allylation reaction using N-propargylated amines, 2,3-dibromopropene, and K2CO3 in DMSO, followed by a CuI-catalyzed [3+2] cycloaddition reaction with sodium azide. These chemicals serve as starting materials and catalysts to facilitate the formation of the desired triazole derivatives with high efficiency and good product yield (80–91%). The study's purpose is to develop a simple, efficient method for synthesizing these compounds, which could be practically useful given their potential broad bioactivities.
The research focuses on the development of a versatile method for nucleoside modification using boron clusters, leveraging the chemical ligation technique based on Huisgen 1,3-dipolar cycloaddition. The purpose of this study is to create new materials with unique physical, chemical, or biological properties by integrating metal and metalloid elements into nucleic acids, which can be applied in fields such as nanobiotechnology, bioelectronics, and biosensing. The researchers synthesized nucleoside conjugates containing carborane and metallocarborane complexes, using terminal azide or ethynyl groups on boron-cluster donors and nucleosides as boron-cluster acceptors. The methodology provides a convenient way to synthesize libraries of boron-cluster-modified nucleosides for various applications, including chemotherapeutics, boron neutron capture therapy (BNCT) of tumors, and as pharmacophors. Key chemicals used in the process include nucleosides with various spacers, boron-cluster donors such as 7,8-dicarba-nido-undecaborate and [3-metal bis(1,2-dicarbollide)]ate ions, and reagents like sodium azide, alkynol-derived alcoholate nucleophiles, and copper(I) catalysts for the click chemistry reactions. The successful synthesis of these conjugates demonstrates the potential of click chemistry in the bioorganic chemistry of boron compounds.
The study focuses on the synthesis of perfluoralkyl isocyanates and 1,1-dihydroperfluoralkyl isocyanates. The research explores the conversion of perfluorocarbon carboxylic acid chlorides to isocyanates via the Curtius rearrangement, involving intermediates such as acid azides. Sodium azide is used to convert acid chlorides to acid azides, which are then converted to isocyanates. The study also investigates the reduction of perfluorocarbon nitriles to amines using lithium aluminum hydride (LiAlH4), which are subsequently phosgenated to form isocyanates. Additionally, the study examines the synthesis of 1,1-dihydroperfluoralkyl amines through the reduction of perfluorocarbon amides with LiAlH4, and their subsequent phosgenation to produce 1,1-dihydroperfluoralkyl isocyanates. The study aims to improve the yields and methods for synthesizing these compounds, which have potential applications in various chemical industries.
The study focuses on synthesizing CuO supported 1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium chloride (MTMSP-Im/Cl) nanoparticles as an efficient, simple, and eco-friendly heterogeneous nanocatalyst for the selective ring opening of epoxides with azide anion in water to produce β-azido alcohols. The CuO nanoparticles serve as the base material for the catalyst, providing a high surface area and reactive morphology. The MTMSP-Im/Cl is grafted onto the CuO nanoparticles to enhance the catalytic activity and facilitate the dispersion of the catalyst in water. Sodium azide acts as the azide anion source to react with epoxides in the presence of the catalyst to form β-azido alcohols. The synthesized nanocatalyst was characterized using various techniques, and it demonstrated high catalytic activity, easy separation, and recyclability for four cycles without significant loss of activity. The study highlights the advantages of this methodology, including excellent regioselectivity, high yields, short reaction times, and simple workup for obtaining products with high purity.
The study focuses on the enantioselective synthesis of a,a-chlorofluoro carbonyl compounds from simple aldehydes or ketones, which can be further transformed into various optically active molecules with fluorinated quaternary carbon centers through nucleophilic substitution. The researchers used racemic a-chloroaldehydes as precursors and synthesized a,a-chlorofluoro aldehydes with high enantioselectivity using N-fluorosuccinimide (NFSI) and an organocatalyst developed by J?rgensen et al. These enantioenriched compounds were then converted into unsymmetrical a,a-chlorofluoro ketones. The study also explored the direct synthesis of a,a-chlorofluoro ketones from a-unsubstituted ketones using chiral a,a-dichloromalonate. The synthesized compounds were successfully subjected to nucleophilic substitution reactions with sodium azide or thiols, yielding the corresponding substituted products without loss of optical purity.
The study focuses on the enzymatic preparation and resolution of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines, which are important heterocyclic amino alcohols found in bioactive natural products and drugs. The researchers utilized Candida antarctica lipases A and B as catalysts in hydrolytic processes to achieve high enantioselectivity for these heterocycles. The study successfully assigned the absolute configurations of the optically pure heterocycles obtained and demonstrated a convenient biocatalytic approach for preparing all isomers of these compounds. The findings have implications for the synthesis of complex molecules with potential biological activities, as well as for applications in organocatalysis and as chiral auxiliaries.
The study in the Journal of Organometallic Chemistry focuses on the direct nucleophilic displacement of halides (chlorine or iodine) in compounds with the formula (Me3Si)3CSiRRX, where R and R represent various organic groups. The researchers investigated the reactions of these compounds with nucleophiles such as KOCN, KSCN, KCN, or NaN3 in different solvents like CH3CN, MeOH, and DMSO, or CH3CN mixed with H2O. The study explores the influence of steric hindrance on the reactivity of silicon centers bearing the bulky trisyl group (Tsi). It was found that by reducing the steric hindrance or using linear nucleophiles, direct bimolecular displacement reactions occur without the observation of rearrangement. The study also successfully synthesized new compounds with different groups and examined their reactivity with the mentioned nucleophiles, providing insights into the ease of reactions on silicon centers bearing the bulky trisyl group.
The research focuses on developing hypercrosslinked polymers (HCPs) containing dimethylformamide (DMF) moieties as alternatives to DMF solvent for azide-based synthesis. The study synthesized HCP-DMF and HCP-DMF-SO3H, which have flexible DMF-like moieties that provide a polar microenvironment for catalysis. The research aimed to replace hazardous DMF solvent with ethanol (EtOH) in the synthesis of benzylic azides and 1,2,3-triazoles, common structures in bioactive molecules. The experiments involved the conversion of NaN3 to benzylic azides and the synthesis of 1,2,3-triazoles using these HCP catalysts in EtOH, avoiding the use of DMF. Analyses included Fourier-transform infrared spectroscopy (FT-IR), fluorescence spectroscopy using Nile red as a probe, thermogravimetric analysis (TGA), solid-state 13C NMR, X-ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM) to characterize the HCP materials. The catalytic performance of the materials was evaluated by monitoring the reaction yields and recyclability of the catalysts.
Avishek Guin, Rahul N. Gaykar, Subrata Bhattacharjee, and Akkattu T. Biju describe a non-transition metal synthetic method for the synthesis of N-H and N-arylbenzotriazoles via a [3+2] cyclization reaction of sodium azide (NaN3) with arynes. The study showed that the use of cesium fluoride (CsF) as a fluorine source in acetonitrile (CH3CN) solution resulted in the selective generation of N-H benzotriazoles, while the use of potassium fluoride (KF) in tetrahydrofuran (THF) solution under open flask conditions resulted in the generation of N-arylbenzotriazoles. The method was optimized to provide high selectivity and yields, with N-H benzotriazoles in 64% yield and N-arylbenzotriazoles in 94% yield. The researchers also explored substrate applicability and successfully synthesized a variety of benzotriazoles containing different arynes. Mechanistic experiments showed that the reaction first proceeded via a [3+2] cyclization reaction followed by an N-arylation reaction, with atmospheric moisture playing an important role in the protonation process.
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