Sodium Hydride Research Articles

Study on Synthesis and Performance of Methyl Diphenyl Urea Stabilizer

Diphenylamine (DPA), formyl chloride, and sodium hydride (NaH) as raw materials synthesize methyldiphenylurea stabilizer by alkylation reaction. The physical and chemical properties of methyldiphenylurea were characterized by nuclear magnetic resonance hydrogen spectrum (1HNMR), X-ray energy spectrum (EDS), Fourier transforms infrared spectroscopy (FT-IR) and differential thermal analysis (DTA). Thermal Decomposition Experiment of Nitrate Propellant Containing Stabilizer by Thermogravimetric Analysis (TGA), exploring the Effect of Different Stabilizers. The molecular surface electrostatic potential energy of methyl diphenyl urea, triphenylamine ( TPA ), dimethyl diphenyl urea (C2), and glycerol trinitrate were calculated by Materials Studio software. The interaction between the stabilizer and glycerol trinitrate molecule was studied. The results showed that the weight loss rate of methyl diphenyl urea was less than 0.1 % within 30 days, and the chemical stability was good. And its negative electrostatic potential energy is larger than that of C2 and TPA, its intermolecular binding ability with glycerol trinitrate is stronger, and its inhibition of nitrate decomposition stability is the best.

Direct insertion into the C–C bond of unactivated ketones with NaH-mediated aryne chemistry

•o-Diiodoarenes/NaH as an efficient system for aryne generation in a controlled manner •Neighboring-group-assisted metal-halogen exchange process •Sodium hydride as an iodophile reagent •Aryne insertion into C–C σ-bond of unactivated ketones Here, we document the reinvention of aryne chemistry with “old” o-diiodoarenes as aryne progenitors. We have established a NaH-mediated activation strategy for the generation of highly reactive aryne species in a controlled manner. The resulting arynes can efficiently participate in a C–C σ-bond-insertion reaction with unactivated ketones, which is difficult to achieve by existing methods. Density functional theory (DFT) calculations reveal that the two adjacent iodines in o-diiodoarenes play critical roles in the formation of aryne. The nucleophilic attack of hydride to the electrophilic iodine requires that the adjacent iodine act as a directing group to accelerate this process, whereas mono-substituted iodobenzene lacking the neighboring-group participation makes it difficult. The in-situ-formed enolates from ketones are proposed to adopt tetrameric aggregates to react with arynes, which accounts for the high regiochemistry for substrates with bulky substituents. Here, we document the reinvention of aryne chemistry with “old” o-diiodoarenes as aryne progenitors. We have established a NaH-mediated activation strategy for the generation of highly reactive aryne species in a controlled manner. The resulting arynes can efficiently participate in a C–C σ-bond-insertion reaction with unactivated ketones, which is difficult to achieve by existing methods. Density functional theory (DFT) calculations reveal that the two adjacent iodines in o-diiodoarenes play critical roles in the formation of aryne. The nucleophilic attack of hydride to the electrophilic iodine requires that the adjacent iodine act as a directing group to accelerate this process, whereas mono-substituted iodobenzene lacking the neighboring-group participation makes it difficult. The in-situ-formed enolates from ketones are proposed to adopt tetrameric aggregates to react with arynes, which accounts for the high regiochemistry for substrates with bulky substituents.

Plasma‐Driven Nitrogen Fixation on Sodium Hydride

AbstractThe development of alternative approaches to the conventional Haber–Bosch ammonia synthesis process is an imperative but very challenging task. Extrinsic stimuli such as plasma could provide greater flexibility in materials selection and process innovation for nitrogen fixation. Hydride (hydrogen anion, H‾)‐containing materials have recently shown promise in thermal ammonia synthesis, whereas the interactions of hydrides and N2 under plasma have rarely been investigated. Herein we explore plasma‐driven nitrogen fixation to NH3 mediated by an inexpensive and common reagent sodium hydride, which does not react with N2 under normal thermal conditions. Nitrogen plasma can produce reactive nitrogen species and also induce the dehydriding of NaH, which result in the activation and hydrogenation of N2 to surface NaNH2 species. The subsequent thermal‐hydrogenation of NaNH2 produces NH3 facilely. The stepwise chemical loop prevents ammonia from plasma‐induced cracking. This NaH‐mediated chemistry broadens the scope of hydrides as well as many other materials for N2 fixation, and also has prospect for other chemical transformations.

Design, Synthesis, In silico ADMET Prediction, Molecular Docking, Antimicrobial and Antioxidant Evaluation of Novel Diethyl Pyridinyl Phosphonate Derivatives

Abstract: A series of new diethyl 4,6-diarylpyridin-2-yl phosphonate derivatives 3a-f, and 5a,b were synthesized, in good yields, from the reaction of 2-bromo-4,6-diarylpyridines 1a,b with Wittig-Horner reagents 2a-c, and 4 in DMF containing sodium hydride at reflux temperature. The newly synthesized compounds were evaluated for antimicrobial and antioxidant activity. The results demonstrated that compounds 5a and 5b exhibited strong antimicrobial activity against S. aureus, E. faecalis, P. aeruginosa, and S. mutans. Compounds (3d, 3e, 3f) exhibited superior antioxidant scavenging activity with DPPH and ABTS activity with values (85.19 ± 0.33, 80.19 ± 0.98, 82.33 ± 0.90) and (70.11 ± 0.98, 63.55 ± 0.80, 69.54 ± 1.02) at concentrations (2.0 mg.ml-1), respectively. The results of the molecular docking simulation indicated that the synthesized compounds displayed lower binding energy with various types of interaction at the active sites of Dihydropteroate synthase, Sortase A, LasR, and Penicillin-binding proteins pockets, suggesting that they could have a potential inhibitory effect on the enzymes and exhibit promising antimicrobial properties. Additionally, the simulation of the active sites of the Peroxidase enzyme as an antioxidant receptor revealed that compounds (5a and 5b) exhibited minimal binding energy and a strong affinity for the active pocket of the peroxidase enzyme.

Design and synthesis optimization of novel diimide indoles derivatives for ameliorating acute lung injury through modulation of NF-κB signaling pathway

Acute lung injury (ALI) is a common respiratory disease caused by local or systemic inflammatory reaction. Based on the natural 7-chain diaryl anti-inflammatory framework, a series of diimide indoles derivatives were designed by combining curcumin and indole in this study. The synthesis of diimide compounds was extended using dichloromethane (DCM) as solvent and 1,1′-carbonyldiimidazole (CDI) and sodium hydride (NaH) as double activators, and a total of 40 diimide-indole derivatives were obtained. The results of in vitro anti-inflammatory activity showed that most compounds could inhibit the production of interleukin-6 (IL-6) better than curcumin and indomethacin. Among the compounds, the IC50 of compound 11f on IL-6 reached 1.05 μM with no obvious cytotoxic side effects. Mechanistically, compound 11f could block the expression of NF-κB P65 phosphorylation, and nuclear translocation of P65. The acute toxicity tests in-vivo also showed no obvious toxicity in mice after the intragastric administration of 1000 mg/kg. In addition, the compound 11f could significantly inhibit the LPS-induced inflammatory response in mice and reduce the number of neutrophils and wet/dry lung weight ratio, thereby alleviating ALI. These results indicated that the novel diimide indoles were promising anti-inflammatory agents for the treatment of ALI.

A Simple and Modified One Pot Conversion of Carboxylic Acid to Ketone

Background: Ketone is one of the important functional groups in synthetic chemistry. For this reason, organic chemists focused on the synthesis of ketone starting from various functionalities since nineties. One of the method deals with the conversion of carboxylic acids to ketones in a one pot manner. We have recently reported a one pot transformation of carboxylic acid to ketone using TsCl or MsCl as an activator of carboxylc acid. In our previous reports, two equivalents of organometallic reagent have been used which may not be useful in medicinal chemistry. In this report, we have developed an alternative process for the transformation where only one equivalent of organometallic reagent has been employed. Objective: In present scenario, we are interested to develop a process for the transformation of carboxylic acid to ketone using one equivalent of an organometallic reagent. Methods: A carboxylic acid reacted with tosyl chloride in the presence of a sodium hydride to form a mixed anhydride. Here, the acidic proton was removed from the reaction mixture as hydrogen gas. This mixed anhydride was then treated with one equivalent of an organomagnesium reagent at -30°C to obtain the desired ketone. Results: Following the optimum conditions, a few commercially available carboxylic acids were treated with TsCl, followed by the treatment of phenyl magnesium and methyl magnesium bromide to obtain phenyl and methyl ketones, respectively, in good to excellent yields. Conclusion: A simple and modified one pot method for the conversion of carboxylic acids to ketone has been reported. In this developed process, one equivalent of the organomagnesium reagent has been used to obtain the desired ketone under the optimized reaction conditions.

Generation of Allylmagnesium Reagents by Hydromagnesiation of 2-Aryl-1,3-dienes.

A protocol for the generation of allylmagnesium reagents from 2-aryl-1,3-dienes was developed using magnesium hydride (MgH2 ) that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2 ) in tetrahydrofuran (THF). Downstream functionalization of the resulting allylmagnesium reagents with carbonyl compounds or alkyl (pseudo)halides delivers branched products having an allylic quaternary carbon center, whereas that with chlorosilanes resulted in formation of linear allylsilanes in regio and stereoselective manners. Further derivatizations of the homoallylic alcohols and allylsilanes were also demonstrated.

Generation of Allylmagnesium Reagents by Hydromagnesiation of 2‐Aryl‐1,3‐dienes

AbstractA protocol for the generation of allylmagnesium reagents from 2‐aryl‐1,3‐dienes was developed using magnesium hydride (MgH2) that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI2) in tetrahydrofuran (THF). Downstream functionalization of the resulting allylmagnesium reagents with carbonyl compounds or alkyl (pseudo)halides delivers branched products having an allylic quaternary carbon center, whereas that with chlorosilanes resulted in formation of linear allylsilanes in regio and stereoselective manners. Further derivatizations of the homoallylic alcohols and allylsilanes were also demonstrated.

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

AbstractAn efficient and convenient palladium-catalyzed reductive system by employing sodium hydride as the hydrogen donor and acetic anhydride as an activator has been developed for transfer hydrogenation and acetylation of a wide range of N-heteroarenes including quinoline, phthalazine, quinoxaline, phenazine, phenanthridine, and indole. Moreover, acridine substrates could be directly reduced without the use of acetic anhydride. This protocol provides a simple method for the preparation of various saturated N-heterocycles.

Nonadiabatic wave packet dynamics and predissociation resonances in sodium hydride.

Vibrational wave packet dynamics provides an opportunity to explore the energy landscape and the population transfer between nonadiabatically coupled excited electronic states. Here the coupled nonadiabatic dynamics of the C1Σ+ and D1Σ+ states of sodium hydride (NaH) in the gas phase in the adiabatic picture is studied, using a sequence of ultra-fast laser pulses in the femtosecond region. Emergence of different population dynamics and dissociation probabilities is shown by carefully choosing the pulse wavelength, duration and time-shift between the pulses, exciting the molecule from the ground X1Σ+ state via the immediate A1Σ+ state. Quantum dynamics simulations were performed in the adiabatic picture, avoiding the adiabatic to diabatic transformation. Predissociation resonances, i.e. vibrational states with finite lifetimes, arise due to nonadiabatic couplings between bound and continuum states. Here accurate resonance energies and widths are computed providing further insight into the dissociation dynamics.

Sequential analysis for identification of byproduct from N-benzylation reaction: wound healing and anti-inflammatory potential of the byproduct 4-chlorobenzyl 2-((4-chlorobenzyl)amino)benzoate.

A very common reaction, N-benzylation of isatoic anhydride in the presence of sodium hydride base, produces byproducts. The yield of one of the byproducts was greater than that of the desired product; therefore, we identified the anonymous undisclosed structure of the byproduct using sequential spectroscopy methods and SC-XRD. This byproduct was found to be effective as a wound-healing and anti-inflammatory agent. The 10% formulation of byproduct and standard (nitrofurazone) showed complete wound closure with a large number of cell migrations within 16 days. Hydroxyproline contents of 5% and 10% formulations were found to be slightly increased as compared with that of the standard. The byproduct also had anti-inflammatory potential. It was effective in inhibiting COX-2, heat-induced albumin denaturation, and formalin-induced paw edema.

In Situ Observation of Electron-Beam-Induced NaH Decomposition in Graphene Nanoreactors by Transmission Electron Microscopy

Sodium hydride (NaH) was unprecedently embedded inside graphene nanobubbles via the discovered reaction between NaH and CO. With the graphene nanobubble as a nanoreactor for NaH, we directly observed the electron-beam-induced decomposition process of graphene-covered NaH by in situ high-resolution transmission electron microscopy with energy dispersive spectrometry and electron energy loss spectroscopy, revealing its decomposition mechanism. This can provide guidance for the design of hydrogen storage materials.

Shaken Not Stirred: Perfluoropyridine-Polyalkylether Prepolymers

The purpose of this work was to employ perfluoropolyalkylethers (PFPAEs) with perfluoropyridines (PFPs) to form telechelic oligomers for use in low-temperature materials. Since perfluoropyridines are very regioselective, various nucleophiles were utilized, starting with an arsenal of PFPAEs such as oligo(hexafluoropropylene oxide) methylene alcohol (Krytox Methylene alcohols), Mach I perfluoroether diol, and Fluorolink E10H. Each reaction was completely successful with PFP using bases such as sodium hydride or the preferred cesium carbonate. Various solvents could be utilized (tetrahydrofuran (THF) or acetonitrile), but dimethylformamide (DMF) was the favored option. Further exploration was accomplished with mechanochemical synthesis, and the majority of the reactions were shortened from their 48 to 72 h reactions to approximately 1 min in good to moderate yields. Finally, Fluorolink E10-H-based bis(perfluoropyridine)-PFPAE was then copolymerized with Bisphenol A, Bisphenol AF, 1,1,1-tris(4-hydroxyphenyl) ethane, and PEG 2000 forming novel materials, which were further characterized with thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS).

Reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione with some phosphorus halides: A simple synthesis of novel 1,2-benzoxaphosphinines

A simple method for design of some novel 1,2-benzoxaphosphinines 2–9, was achieved. The methodology depended on cyclization of 1-(2-hydroxy-phenyl)-3-phenylpropane-1,3-dione (1) as starting material with some phosphorus halides in dry solvent in the presence of a base. Reaction of the substrate 1 with some phosphorus halides, such as P,P-dichlorophenylphosphine, phenyl phosphonic dichloride, phenyl phosphorodichloridate, and phosphorus oxychloride in dry toluene containing triethylamine led to a predominant formation of 3-benzoyl-4-hydroxy-2H-1,2-benzoxaphosphinines 2–5, respectively. Under the same reaction conditions, the molecular structures of type 3-benzoyl-4H-1,2-benzoxaphosphinin-4-ones 6 and 7 were isolated by treatment of the substrate 1 with phosphorus pentachloride and phosphorus tribromide, respectively. In addition, the interesting 4-(1-phenyl-ethanoyl)-1,2,λ5-benzoxaphosphinines 8 and 9 were obtained by treatment of compound 1 with acetonyl and benzyl triphenylphosphonium chlorides, respectively, in dry dioxane and sodium hydride. The chemical structures of the title compounds were established by elemental analysis and spectral tools.

A novel synthetic approach to Pyrazolooxazines. One‐pot synthesis of Pyrazolo[5,1‐c][1,4]oxazine derivatives from 2,2‐dichlorovinylacetophenones

AbstractNew convenient synthetic methods in pyrazoline and pyrazolooxazine chemistry have been developed starting from 2,2‐dichlorovinylacetophenones 4, whose reaction with 2‐hydroxyethylhydrazine directly gave hitherto unknown 3‐aryl‐5‐dichloromethyl‐1‐(2‐hydroxiethyl)‐2‐pyrazolines 7 in high yields. These were found to be able to undergo cyclization to afford 2‐aryl‐6,7‐dihydro‐4H‐pyrazolo[5,1‐c][1,4]oxazines 10 upon treatment with sodium hydride. Compounds 10 could also easily be obtained in near quantitative yields by a one‐pot preparative process involving reaction of compounds 4 with 2‐hydroxyethylhydrazine followed by addition of sodium hydroxide. The simplicity and the high yield of this reaction make it much more attractive than the previously described multistep procedure. The molecular structure of 2‐(4‐chlorophenyl)‐6,7‐dihydro‐4H‐pyrazolo[5,1‐c][1,4]oxazine 10c was determined by x‐ray crystallography.

An Improved Scalable Synthesis of the Potent Antiviral (S)-HPMPA.

We present an improved synthesis of (S)-HPMPA (1) from an easily accessible and commercially available compound, (S)-3-(benzyloxy)propane-1,2-diol (10). Tritylation of primary alcohol 10 was highly selective, and pure product was isolated in good yield. Alkylation of (R)-1-(benzyloxy)-3-(trityloxy)propan-2-ol (11) with diethyl p-toluenesulfonyloxymethyl phosphonate (6) using sodium hydride in tetrahydrofuran followed by detritylation afforded the desired chiral synthon 12. Tosylation of the primary alcohol and subsequent reaction with sodium adeninate afforded protected S-HPMPA (14). Global deprotection using concentrated hydrochloric acid in a sealed tube afforded S-HPMA (1), and the deprotected 1 was crystallized from water and acetone to obtain a 99% pure product. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Preparation of (R)-1-(benzyloxy)-3-(trityloxy)propan-2-ol (11) Basic Protocol 2: Preparation of diethyl (S)-(((1-(benzyloxy)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate (12) Basic Protocol 3: Preparation of (R)-3-(benzyloxy)-2-((diethoxyphosphoryl)methoxy)propyl-4-methylbenzenesulfonate (13) Basic Protocol 4: Preparation of diethyl (S)-(((1-(6-amino-9H-purin-9-yl)-3-(benzyloxy)propan-2-yl)oxy)methyl)phosphonate (14) Support Protocol 1: Preparation of sodium adeninate Basic Protocol 5: Preparation of (S)-(((1-(6-amino-9H-purin-9-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid (1).

Production and characterization of hierarchical zeolite Y catalyst for biodiesel production using waste cooking oil as a feedstock

This study reports the production and characterization of hierarchical zeolite Y (HZY) catalyst from commercial zeolite Y (CZY) for biodiesel using waste cooking oil as feedstock. The hierarchical zeolite Y catalyst produce were characterized using X-Ray diffraction (XRD), scanning electron microscopy (SEM) and Brunnauer, Emmeitt and Teller(BET) analysis. From the BET results of hierarchical Y zeolite produced shows that mole concentration of simultaneous desilication and mild dealumination determine the hierarchical factor of the produced hierarchical Y zeolite. Furthermore, this process was optimized by varying both the mole concentration aqueous solutions of Sodium Hydrides (NaOH) and Ethylenediaminetetraacetic acid (H4EDTA). The two process variables NaOH and H4EDTA were found to be statistically significant for high surface area, pore volume and pore size whereby, the value obtained for surface area are 193.83, 216.03, 212.34 and 218.33 m2/g while the hierarchy factor was calculated to be 0.0571, 0.1540, 0.1781 and 0.1042 respectively. The highest value of hierarchy factor (0.1781) of hierarchical zeolite Y sample (HZY-3) occur at 0.3 M of NaOH and 0.3 M of H4EDTA with a pore volume of 0.3785 c m3/g and a pore size of 8.5512 nm, which represent the most suitable for optimum reactivity compared to others. The XRD of hierarchical zeolite Y shows a slight decrease in the peak intensity which is associated with partial extraction of Si and Al from the zeolite framework during alkaline-to-acid treatment. Some peaks were also formed which show that the level of crystallinity has increased while the SEM/EDX determined the crystallite size and the morphology. From the EDX, the hierarchical zeolite Y Si/Al ratio was calculated to be 15.0. HZY gave a biodiesel yield of 94.8% at 55 °C for 90 mins while CZY gave a yield of 62.00% at the same condition. A reusability test was also carried out and it was observed that at repeated 5th runs, biodiesel yield using the same HZY catalyst dropped to 83% which was still reasonable enough compared to the CZY catalyst which was observed to have dropped to 41%. This indicates that the hierarchy factor of the HZY catalyst produced decides the activity of solid catalysts in biodiesel production.

Preparationandinhibitoryeffectofsalicin dimethyl etherinLaryngealcancercellsthrough theapoptosisactivation.

Laryngeal cancer is detected commonly worldwide, and it ranks second highest in incidence among the respiratory tract neoplasms following only head and neck squamous cell cancer. In the present study salicin dimethyl ether was synthesized and evaluated against laryngeal cancers cells for anticancer property. MTT assay was used for the measurement of changes in TU686 and Tu212 cell proliferation while as induced apoptosis was detected by flow cytometry. Protein expression was determined by western blotting and expression of mRNA by RT-PCR assay. In the present study salicin dimethyl ether was synthesized by the reaction of salicin with methyl iodide using sodium hydride as base. Salicin dimethyl ether treatment led to a significant decrease in TU686 and Tu212 cell proliferation in a dose-dependent manner. In TU686 and Tu212 cells salicin dimethyl ether treatment caused a significant increase in cell apoptosis and elevated caspase-3 activity. Treatment with salicin dimethyl ether led to a prominent reduction in Bcl-2 protein expression in TU686 and Tu212 cells at 72 h. Salicin dimethyl ether treatment led to a prominent decrease in p-PI3K and p-Akt protein expression in TU686 and Tu212 cells, compared to the untreated cells. A significant increase in miR‑15a expression in TU686 and Tu212 cells was observed on treatment with salicin dimethyl ether at 72 h. In summary, the current study demonstrates that salicin dimethyl ether, a synthetic derivative of salicin, suppresses proliferation of TU686 and Tu212 cells. The underlying mechanism involves induction of apoptosis, inhibition of PI3K/Akt pathway and promotion of miR-15a expression. Therefore, salicin dimethyl ether may be used for inhibition of laryngeal cancer growth, however, in vivo studies need to be conducted to confirm the effect.

Molecular structure, spectral and theoretical study of new type bile acid–sterol conjugates linked via 1,2,3-triazole ring

New six steroid conjugates have been prepared from bile acids (tail part)and sterol (head part) derivatives using click chemistry method. The azide-alkyne Huisgen cycloaddition (intermolecular 1,3-dipolar cycloaddition) of the azide derivatives of lithocholic, deoxycholic, cholic acid and propiolate ester of cholesterol and cholestanol gave a new bile acid–sterol conjugates linked with a 1,2,3-triazole ring. Previously, bile acids were converted into bromoacetyl substituted derivatives by the reaction of propargyl esters of lithocholic, deoxycholic, cholic with bromoacetic acid bromide in toluene with TEBA and sodium hydride. Additionally, five of the reagents: bromoacetyl and azidoacetyl substituted derivatives of propargyl esters of deoxycholic and cholic acids as well as 5α-cholestan-3-yl-propynoatewere also obtained and characterized for the first time. All conjugates were obtained in good yields using an efficient synthesis method. The structures of all conjugates as well as four substrates were confirmed by spectral (1H- and 13C NMR, and FT-IR) analysis, mass spectrometry (ESI-MS), as well as PM5 semiempirical methods. Also B3LYP calculations have been carried out. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6–311G(d,p) approach and analyzed. Theoretical vibrational parameters are compared with obtained experimental parameters. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS). Additionally molecular docking was performed for the selected conjugate.

Amination of epoxides as a convenient approach for lipophilic polyamines synthesis

Objectives. Alkylated derivatives of polyamines are able to block the growth of cancer cells due to their embedding into the polyamine biosynthesis mechanisms. The study aimed to synthesize lipophilic derivatives of norspermine or triethylenetetramine based on the formation of a C–N bond during the opening of the oxirane ring by primary amines to expand a number of synthetic polyamine derivatives with antitumor activity.Methods. The starting compounds—glycidol alcoholate or epichlorohydrin—were reacted with hexadecyl bromide or sodium hexadecanolate to give glycidyl hexadecyl ether. The key reaction for the preparation of lipophilic polyamines was the amination of lipophilic epoxides with polyamines in the presence of calcium triflate. Acylation of the hydroxyl group formed during the opening of oxirane was carried out by the action of 4-dimethylaminopyridine and acetic anhydride. The introduction of an alkyl substituent in the presence of sodium hydride led to intramolecular cyclization with the formation of an oxoazolidine cycle. The regioselectivity of the oxirane ring opening reaction at the C(1) position of glycerol was confirmed by two-dimensional heteronuclear {1H,13C} nuclear magnetic resonance spectroscopy.Results. An approach to the synthesis of novel lipophilic polyamines based on the catalytic amination of epoxides was developed and tested. Compounds based on norspermine and triethylentetramine containing a hydroxyl group at the C(2) atom of the glycerin backbone were obtained. For norspermine derivatives, the hydroxyl group was modified: an acetyl substituent was introduced and a derivative containing an oxoazolidine cycle was obtained.Conclusions. The obtained lipophilic polyamines can be considered as potential antitumor agents, for which cytotoxicity against various cancer cells will be evaluated in the future.