Recent Advances in Design, Synthesis, and Biological Activity Studies of 1,3-Selenazoles.

The review examines recent advances in the design and synthesis of 1,3-selenazole derivatives since 2000. Various synthetic approaches to 1,3-selenazoles and reaction conditions are discussed. The beneficial properties of 1,3-selenazoles, especially their biological activity, are emphasized.

Selenium Dibromide Click Chemistry: The Efficient Synthesis of Novel Selenabicyclo[3.3.1]nonene-2 and -nonane Derivatives.

Highly efficient and convenient methods for the preparation of 35 novel derivatives of 9-selenabicyclo[3.3.1]nonane and 9-selenabicyclo[3.

Recent Advances in Design and Synthesis of Diselenafulvenes, Tetraselenafulvalenes, and Their Tellurium Analogs and Application for Materials Sciences.

The first organic metals were obtained based on tetrathiafulvalene. The most significant advance in the field of organic metals was the discovery of superconductivity. The first organic superconductors were obtained based on tetramethyltetraselenafulvalene.

Deep Neural Network Recognition of Rivet Joint Defects in Aircraft Products.

The mathematical statement of the problem of recognizing rivet joint defects in aircraft products is given. A computational method for the recognition of rivet joint defects in aircraft equipment based on video images of aircraft joints has been proposed with the use of neural networks YOLO-V5 for detecting and MobileNet V3 Large for classifying rivet joint states. A novel dataset based on a real physical model of rivet joints has been created for machine learning.

Clathrate Hydrates of Organic Solvents as Auxiliary Intermediates in Pharmaceutical Research and Development: Improving Dissolution Behaviour of a New Anti-Tuberculosis Drug, Perchlozon.

There is an urgent need for new drugs to overcome the challenge of the ever-growing drug resistance towards tuberculosis. A new, highly efficient anti-tuberculosis drug, Perchlozone (thioureidoiminomethylpyridinium perchlorate, Pz), is only available in an oral dosage form, though injectable forms and inhalation solutions could be better alternatives, offering higher bioavailability. To produce such forms, nano- and micro-particles of APIs would need to be prepared as dispersions with carriers.

Selenium Dihalides Click Chemistry: Highly Efficient Stereoselective Addition to Alkynes and Evaluation of Glutathione Peroxidase-Like Activity of Bis(-2-halovinyl) Selenides.

Highly efficient stereoselective syntheses of novel bis(-2-chlorovinyl) selenides and bis(-2-bromovinyl) selenides in quantitative yields by reactions of selenium dichloride and dibromide with alkynes were developed. The reactions proceeded at room temperature as -addition giving products exclusively with ()-stereochemistry. The glutathione peroxidase-like activity of the obtained products was estimated and compounds with high activity were found.

Quantum Chemical and Experimental Studies of an Unprecedented Reaction Pathway of Nucleophilic Substitution of 2-Bromomethyl-1,3-thiaselenole with 1,3-Benzothiazole-2-thiol Proceeding Stepwise at Three Different Centers of Seleniranium Intermediates.

The results of quantum chemical and experimental studies of the reaction of 2-bromomethyl-1,3-thiaselenole with 1,3-benzothiazole-2-thiol made it possible to discover the unprecedented pathway of this reaction, which proceeds stepwise at three different centers of seleniranium intermediates. The first stage includes an attack of thiolate anion at the selenium atom of the seleniranium cation accompanied by ring opening with the formation of (Z)-2-[(1,3-benzothiazol-2-ylsulfanyl)selanyl]ethenyl vinyl sulfide, which is converted to six-membered heterocycle, 2-(2,3-dihydro-1,4-thiaselenin-2-ylsulfanyl)-1,3-benzothiazole, in a 99% yield. The latter compound undergoes rearrangement with ring contraction producing five-membered heterocycle, 2-[(1,3-thiaselenol-2-ylmethyl)sulfanyl]-1,3-benzothiazole, in a 99% yield (the thermodynamic product).

A Novel Family of [1,4]Thiazino[2,3,4-]quinolin-4-ium Derivatives: Regioselective Synthesis Based on Unsaturated Heteroatom and Heterocyclic Compounds and Antibacterial Activity.

A novel family of [1,4]thiazino[2,3,4-]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group.

Peculiarities and Applications of Stochastic Processes with Fractal Properties.

In this paper, the fractal properties of stochastic processes and objects in different areas were specified and investigated. These included: measuring systems and sensors, navigation and motion controls, telecommunication systems and networks, and flaw detection technologies. Additional options that occur through the use of fractality were also indicated and exemplified for each application.

Efficient Regioselective Synthesis of Novel Condensed Sulfur-Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes.

The preparation of novel reagents 2-quinolinesulfenyl chloride and bromide based on available 2-mercaptoquinoline has been described. This approach opens up opportunities for the introduction of 2-quinolinesulfenyl chloride and bromide into organic synthesis. Regioselective synthesis of novel 1,2-dihydro[1,3]thiazolo[3,2-]quinolin-10-ium derivatives in high yields has been developed by annulation reactions of 2-quinolinesulfenyl chloride and bromide with alkenes.

A Regioselective Synthesis of Novel Functionalized Organochalcogen Compounds by Chalcogenocyclofunctionalization Reactions Based on Chalcogen Halides and Natural Products.

The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium dibromide with allyl thymol and allyl carvacrol proceeded in methylene chloride at room temperature in the presence of NaHCO affording bis[(7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] and bis[(4-isopropyl-7-methyl-2,3-dihydro-1-benzofuran-2-yl)methyl] selenides in 90-92% yield. Similar sulfides were obtained in 70-72% yields by the reaction of sulfur dichloride in chloroform under reflux.

Efficient Synthesis of a New Family of 2,6-Disulfanyl-9-selenabicyclo[3.3.1]nonanes.

The efficient synthesis of a new family of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes in high yields has been developed based on 9-selenabicyclo[3.

Efficient Regioselective Synthesis of Novel Water-Soluble 2,3-[1,4]thiazino[2,3,4-]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides.

Regioselective synthesis of novel 2,3-[1,4]thiazino[2,3,4-]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied.

(,)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides.

The efficient regio- and stereoselective synthesis of (,)-3,3'-selanediylbis(2-propenamides) in 76-93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides. (,)-3,3'-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single representative of 3,3'-selanediylbis(2-propenamides) has been described in the literature.

Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction.

The reaction of 2-(bromomethyl)-1,3-thiaselenole with potassium selenocyanate proceeded via a rearrangement with ring expansion, leading to a six-membered 2,3-dihydro-1,4-thiaselenin-2-yl selenocyanate (kinetic product) which in turn underwent rearrangement with ring contraction to a 1,3-thiaselenol-2-ylmethyl selenocyanate (thermodynamic product). These rearrangements occurred by a nucleophilic attack of the selenocyanate anion at two different carbon atoms of the seleniranium intermediate. The efficient regioselective synthesis of alkyl, allyl, 2-propynyl, benzyl, 4-fluorobenzyl, and 2-pyridinylmethyl 1,3-thiaselenol-2-ylmethyl selenides was developed based on the generation of sodium 1,3-thiaselenol-2-ylmethylselenolate from 1,3-thiaselenol-2-ylmethyl selenocyanate or bis(1,3-thiaselenol-2-ylmethyl) diselenide followed by nucleophilic substitution reactions.

Natural Compounds and Their Structural Analogs in Regio- and Stereoselective Synthesis of New Families of Water-Soluble 2,3-[1,3]thia- and -Selenazolo[3,2-]pyridin-4-ium Heterocycles by Annulation Reactions.

It has been found that both eugenol and isoeugenol derivatives reacted with 2-pyridinesulfenyl and 2-pyridineselenenyl halides in a regioselective mode affording products with opposite regiochemistry. Synthesis of new families of 2,3-[1,3]thia- and -selenazolo[3,2-]pyridin-4-ium heterocycles has been developed by annulation reactions of 2-pyridinechalcogenyl halides with natural compounds (eugenol, isoeugenol, methyl eugenol, methyl isoeugenol, acetyl eugenol, trans-anethole) and their structural analogs. The influence of the substrate structure and the nature of halogen on the product yields are studied.

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes.

The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile.

First example of a high-level correlated calculation of the indirect spin-spin coupling constants involving tellurium: tellurophene and divinyl telluride.

This paper documents the very first example of a high-level correlated calculation of spin-spin coupling constants involving tellurium taking into account relativistic effects, vibrational corrections and solvent effects for medium sized organotellurium molecules. The (125)Te-(1)H spin-spin coupling constants of tellurophene and divinyl telluride were calculated at the SOPPA and DFT levels, in good agreement with experimental data. A new full-electron basis set, av3z-J, for tellurium derived from the "relativistic" Dyall's basis set, dyall.

Open-chain unsaturated selanyl sulfides: stereochemical structure and stereochemical behavior of their 77Se-1H spin-spin coupling constants.

Stereochemical structure of nine Z-2-(vinylsulfanyl)ethenylselanyl organyl sulfides has been investigated by means of experimental measurements and second-order polarization propagator approach calculations of their (1)H-(1)H, (13)C-(1)H, and (77)Se-(1)H spin-spin coupling constants together with a theoretical conformational analysis performed at the MP2/6-311G** level. All nine compounds were shown to adopt the preferable skewed s-cis conformation of their terminal vinylsulfanyl group, whereas the favorable rotational conformations with respect to the internal rotations around the C-S and C-Se bonds of the internal ethenyl group are both skewed s-trans. Stereochemical trends of (77)Se-(1)H spin-spin coupling constants originating in the geometry of their coupling pathways and the selenium lone pair effect were rationalized in terms of the natural J-coupling analysis within the framework of the natural bond orbital approach.

Synthesis of novel E-2-chlorovinyltellurium compounds based on the stereospecific anti-addition of tellurium tetrachloride to acetylene.

The reaction of tellurium tetrachloride with acetylene proceeds in a stereospecific anti-addition manner to afford the novel products E-2-chlorovinyltellurium trichloride and E,E-bis(2-chlorovinyl)tellurium dichloride. Reaction conditions for the selective preparation of each of these products were found. The latter was obtained in 90% yield in CHCl(3) under a pressure of acetylene of 10-15 atm, whereas the former product was formed in up to 72% yield in CCl(4) under a pressure of acetylene of 1-3 atm.

Thia-, aza-, and selena[3.3.1]bicyclononane dichlorides: rates vs internal nucleophile in anchimeric assistance.

Sulfur-, selenium-, and nitrogen-containing compounds bearing leaving groups in the β-position undergo facile substitution chemistry enabled by anchimeric assistance. Here we provide direct comparisons between such systems in the rigid bicyclo[3.3.

Conformational analysis and diastereotopic assignments in the series of selenium-containing heterocycles by means of 77Se-1H spin-spin coupling constants: a combined theoretical and experimental study.

A combined theoretical and experimental study on the stereochemical behavior of (77)Se-(1)H spin-spin coupling constants has been performed at the second-order polarization propagator approach level together with heteronuclear multiple-bond correlation technique in the series of selenium-containing four-, five- and six-membered heterocycles including the derivatives of thiaselenetane, selenasilole, thiaselenole, thiaselenolane and dihydrothiaselenine. Geminal and vicinal (77)Se-(1)H spin-spin couplings were shown to have the pronounced stereochemical dependences in respect with the topology of the coupling pathway, internal rotation of the side-chain substituents and ring inversion providing a straightforward tool for the conformational analysis and diastereotopic assignments in the chiral organoselenium compounds.

Divinyl selenide: conformational study and stereochemical behavior of its 77Se-1H spin-spin coupling constants.

Theoretical energy-based conformational analysis of divinyl selenide performed at the MP2/6-311G** level is substantiated by the second-order polarization propagator approach (SOPPA) calculations and experimental measurements of its (77)Se-(1)H spin-spin coupling constants, demonstrating marked stereochemical behavior in respect of the internal rotation of both vinyl groups around the Se-C bonds. Based on these data, divinyl selenide is shown to exist in an equilibrium mixture of three nonplanar conformers: one the preferred syn-s-cis-s-trans and two minor anti-s-trans-s-trans and syn-s-trans-s-trans forms.

[The antiradiation activity and mechanism of action of dimethylaminodithiazines].

A new group of radioprotective agents, dimethylaminodithiazines, was discovered. The agents are effective when used in relatively small amounts and exert a radioprotective effect rapidly with both intraperitoneal and per os injections. The role of inhibition of oxidative processes and DNA biosynthesis in the mechanism of radioprotective action of dimethylaminodithiazines is discussed.