121 research outputs found

    The Operationalization of Task Goal Difficulty: An Exploration of Qualitative and Quantitative Methods

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    This study contributed to an understanding of the goal setting process by investigating a variety of ways to evaluate the difficulty of short-term goals, including requested quantitative goals, different methods to rate the difficulty of self-defined goals, and the difficulty perceptions of the goal-setters themselves. To examine the validity of different goal-difficulty assessment strategies, I collected short-term academic goals from 116 freshman college students at the beginning of their first semester in college. I also collected antecedents of goal difficulty, such as prior performance and self-efficacy, and collected academic achievement at the conclusion of that semester. The validity of eight different measures of goal difficulty was examined through the examination of goal-difficulty measures with antecedents and academic performance. Correlations among goal-difficulty measures ranged from weak to strong. Patterns of correlations should encourage the future use of both quantitative goal measures and ratings of self-reported goals. Criterion GPA correlated most strongly with the GPA based assessments of goal difficulty. Goal-setters’ perceived difficulty of goals was not associated with predictors and criteria as goal-theory suggested. Applications, future research directions, and study limitations were discussed

    Composite superconducting wires obtained by high-rate tinning in molten Bi-Pb-Sr-Ca-Cu-O system

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    The preparation of high-T(sub c) superconducting long composite wires by short-time tinning of the metal wires in a molten Bi-Pb-Sr-Ca-Cu-O compound is discussed. The application of this method to the high-T(sub c) materials is tested, possibly for the first time. The initial materials used for this experiment were ceramic samples with nominal composition Bi(1.5)Pb(0.5)Sr2Ca2Cu3O(x) and T(sub c) = 80 K prepared by the ordinary solid-state reaction, and industrial copper wires from 100 to 400 microns in diameter and from 0.5 to 1 m long. The continuously moving wires were let through a small molten zone (approximately 100 cubic mm). The Bi-based high-T(sub c) ceramics in a molten state is a viscous liquid and it has a strongly pronounced ability to spread on metal wire surfaces. The maximum draw rate of the Cu-wire, at which a dense covering is still possible, corresponds to the time of direct contact of wire surfaces and liquid ceramics for less than 0.1 s. A high-rate draw of the wire permits a decrease in the reaction of the oxide melt and Cu-wire. This method of manufacture led to the fabrication of wire with a copper core in a dense covering with uniform thickness of about h approximately equal to 5 to 50 microns. Composite wires with h approximately equal to 10 microns (h/d approximately equal to 0.1) sustained bending on a 15 mm radius frame without cracking during flexing

    Research on Inner Surface of Tubes Hydroformed

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    In this paper is presented a reserch regarding the surfece of hydroforming tubs, made by aluminium and cooper. Hydroforming tubes is very important production method considering that metal tubes are widely used in a great variety of engineering products, such as automobile, aircraft, air conditioner, air compressor, exhaust systems, fluid lines. The results show that the surface of tubes it is influence of the hydroforming process. Also it is very important the material of the tube in research of surface

    Polyfunctional Imidazoles: VIII.* 1-Aryl-4-chloro- 5-[R-sulfanyl(R-sulfonyl)methyl]-1H-imidazoles

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    Alkylation of (1-aryl-4-chloro-1H-imidazol-5-yl)methanethiols with alkyl halides, propargyl bromide, or chloroacetic acid gave 1-aryl-5-(R-sulfanylmethyl)-4-chloro-1H-imidazoles. 1-Aryl-4-chloro-5-(methylsulfanylmethyl)-1H-imidazoles and [(1-aryl-4-chloro-1H-imidazol-5-yl)methylsulfanyl]acetic acids were oxidized to the corresponding sulfones with potassium permanganate.ΠšΠ°Ρ„Π΅Π΄Ρ€Π° Ρ„Π°Ρ€ΠΌΠ°Ρ†Ρ–

    Artificial Neural Networks Model for Springback Prediction in the Bending Operations

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    The aim of this paper is to develop an Artificial Neural Network (ANN) model for springback prediction in the free cylindrical bending of metallic sheets. The proposed ANN model was developed and tested using the Matlab software. The input parameters of the proposed ANN model were the sheet thickness, punch radius, and coefficient of friction. The resulting data is represented by the springback coefficient. Preparation, assessing and confirmation of the model were achieved using 126 data series obtained by Finite element analysis (FEA). ANN was trained by Levenberg - Marquardt back - propagation algorithm. The performance of the ANN model was evaluated using statistic measurements. The predictions of the ANN model, regarding FEA, had quite low root mean squared error (RMSE) values and the model performed well with the coefficient of determination values. This shows that the developed ANN model leads to the idea of being used as an instrument for springback prediction

    Virtual Prototyping : first practice of a European research group

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    Lien vers la version Γ©diteur: http://www.inderscience.com/books/index.php?action=record&rec_id=696&chapNum=5&journalID=1021&year=2009International audienceThe EMIRAcle association has been created as a European association in order to refer as a pool of European experts with respect to design and manufacturing scientific research. A group of EMIRAcle partners have been working on "Virtual Prototyping (VP)" competencies. The long terms main objectives were: To set a common understanding concerning virtual prototyping To gather competencies in Virtual Prototyping including maturityregarding new concepts and software demonstrators To provide to academics or industries methods, models and software tosupport Virtual Prototyping The paper aims at presenting first results of that research group concerning the creation of a VP knowledge map (second objective). Those results are based on a design case study led by several partners of the EMIRAcle association

    2-Π°ΠΌΡ–Π½ΠΎ-5-(4-Ρ…Π»ΠΎΡ€ΠΎ-1Π½-Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»-5-Ρ–Π»)-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»ΠΈ: синтСз, ΠΏΡ–Ρ€ΠΈΠΌΡ–Π΄ΠΎΠ°Π½Π΅Π»ΡŽΠ²Π°Π½Π½Ρ Ρ‚Π° Π±Π°ΠΊΡ‚Π΅Ρ€ΠΈΡ†ΠΈΠ΄Π½Π° Π°ΠΊΡ‚ΠΈΠ²Π½Ρ–ΡΡ‚ΡŒ

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    This investigation is devoted to the synthesis of new representatives of 2-amino-5-imidazolil-1,3,4-thiadiazole systems, the study of some chemical transformations and the bactericidal activity. It has been shown that thiosemicarbazones obtained by condensation of 4-chloro-1H-5-formylimidazoles with thiosemicarbazide when heated with a triple surplus of iron (III) chloride hexahydrate in 80% acetate acid undergo oxidative cyclization with formation of new 2-amino-5-(4-chloroimidazole-5-yl)-1,3,4-thiadiazoles. The compounds synthesized are heterocyclic systems with two electrophilic centres that are widely used when obtaining biheterocyclic biologically active systems. While studying the chemical behaviour of 2-amino-1,3,4-thiadiazoles under research in reactions of annulation with series of bielectrophilic reagents it has been found that they do not react either with phenacylbromide or malononitrile, and with chloroacetylchloride the product of 5-aminoacylation is formed; it even when heated in the boiling DMF in the presence of K2CO3 is not prone to intramolecular cyclocondensation. At the same time heating of 2-amino-1,3,4-thiadiazoles with diethyl ether of acetylenedicarboxylic acid in the absolute boiling ethanol leads to formation of ethyl-7-oxo-[1,3,4]-thiadiazolo-[3,2-a]-pyrimidine-5-carboxylates. The results of studying the antibacterial properties of 2-amino-1,3,4-thiadiazoles have shown that the compounds synthesized possess a moderate bactericidal and fungicidal activity.ИсслСдованиС посвящСно синтСзу Π½ΠΎΠ²Ρ‹Ρ… прСдставитСлСй 2-Π°ΠΌΠΈΠ½ΠΎ-5-ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΈΠ»-1,3,4-Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»ΡŒΠ½Ρ‹Ρ… систСм, ΠΈΠ·ΡƒΡ‡Π΅Π½ΠΈΡŽ Π½Π΅ΠΊΠΎΡ‚ΠΎΡ€Ρ‹Ρ… ΠΈΡ… химичСских ΠΏΡ€Π΅Π²Ρ€Π°Ρ‰Π΅Π½ΠΈΠΉ ΠΈ Π±Π°ΠΊΡ‚Π΅Ρ€ΠΈΡ†ΠΈΠ΄Π½ΠΎΠΉ активности. Показано, Ρ‡Ρ‚ΠΎ тиосСмикарбазоны, ΠΏΠΎΠ»ΡƒΡ‡Π΅Π½Π½Ρ‹Π΅ кондСнсациСй 4-Ρ…Π»ΠΎΡ€-1Н-5-Ρ„ΠΎΡ€ΠΌΠΈΠ»ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² с тиосСмикарбазидом, ΠΏΡ€ΠΈ Π½Π°Π³Ρ€Π΅Π²Π°Π½ΠΈΠΈ с 3-ΠΊΡ€Π°Ρ‚Π½Ρ‹ΠΌ ΠΈΠ·Π±Ρ‹Ρ‚ΠΊΠΎΠΌ гСксагидрата Ρ…Π»ΠΎΡ€ΠΈΠ΄Π° ΠΆΠ΅Π»Π΅Π·Π° (III) Π² 80%-Π½ΠΎΠΉ уксусной кислотС ΠΏΠΎΠ΄Π΄Π°ΡŽΡ‚ΡΡ ΠΎΠΊΠΈΡΠ»ΠΈΡ‚Π΅Π»ΡŒΠ½ΠΎΠΉ Ρ†ΠΈΠΊΠ»ΠΈΠ·Π°Ρ†ΠΈΠΈ с ΠΎΠ±Ρ€Π°Π·ΠΎΠ²Π°Π½ΠΈΠ΅ΠΌ Π½ΠΎΠ²Ρ‹Ρ… 2-Π°ΠΌΠΈΠ½ΠΎ-5-(4-Ρ…Π»ΠΎΡ€ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»-5-ΠΈΠ»)-1,3,4-Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»ΠΎΠ². Π‘ΠΈΠ½Ρ‚Π΅Π·ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹Π΅ соСдинСния относятся ΠΊ гСтСроцикличСским систСмам с двумя ΡΠ»Π΅ΠΊΡ‚Ρ€ΠΎΡ„ΠΈΠ»ΡŒΠ½Ρ‹ΠΌΠΈ Ρ†Π΅Π½Ρ‚Ρ€Π°ΠΌΠΈ, ΠΊΠΎΡ‚ΠΎΡ€Ρ‹Π΅ часто ΠΈΡΠΏΠΎΠ»ΡŒΠ·ΡƒΡŽΡ‚ΡΡ ΠΏΡ€ΠΈ ΠΏΠΎΠ»ΡƒΡ‡Π΅Π½ΠΈΠΈ бигСтСроцикличСских биологичСски Π°ΠΊΡ‚ΠΈΠ²Π½Ρ‹Ρ… систСм. ΠŸΡ€ΠΈ ΠΈΠ·ΡƒΡ‡Π΅Π½ΠΈΠΈ химичСского повСдСния исслСдуСмых 2-Π°ΠΌΠΈΠ½ΠΎ-1,3,4-Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»ΠΎΠ² Π² рСакциях аннСлирования с рядом Π±ΠΈΡΠ»Π΅ΠΊΡ‚Ρ€ΠΎΡ„ΠΈΠ»ΡŒΠ½Ρ‹Ρ… Ρ€Π΅Π°Π³Π΅Π½Ρ‚ΠΎΠ² ΠΎΠ±Π½Π°Ρ€ΡƒΠΆΠ΅Π½ΠΎ, Ρ‡Ρ‚ΠΎ ΠΎΠ½ΠΈ Π½Π΅ Ρ€Π΅Π°Π³ΠΈΡ€ΡƒΡŽΡ‚ Π½ΠΈ с Ρ„Π΅Π½Π°Ρ†ΠΈΠ»Π±Ρ€ΠΎΠΌΠΈΠ΄ΠΎΠΌ, Π½ΠΈ с ΠΌΠ°Π»ΠΎΠ½ΠΎΠ½ΠΈΡ‚Ρ€ΠΈΠ»ΠΎΠΌ, Π° с Ρ…Π»ΠΎΡ€Π°Ρ†Π΅Ρ‚ΠΈΠ»Ρ…Π»ΠΎΡ€ΠΈΠ΄ΠΎΠΌ образуСтся ΠΏΡ€ΠΎΠ΄ΡƒΠΊΡ‚ 5-аминоацилирования, ΠΊΠΎΡ‚ΠΎΡ€Ρ‹ΠΉ Π΄Π°ΠΆΠ΅ ΠΏΡ€ΠΈ Π½Π°Π³Ρ€Π΅Π²Π°Π½ΠΈΠΈ Π² кипящСм Π”ΠœΠ€Π Π² присутствии K2CO3 Π½Π΅ подвСргаСтся внутримолСкулярной циклокондСнсации. Π’ Ρ‚ΠΎ ΠΆΠ΅ врСмя Π½Π°Π³Ρ€Π΅Π²Π°Π½ΠΈΠ΅ 2-Π°ΠΌΠΈΠ½ΠΎ-1,3,4-Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»ΠΎΠ² с диэтиловым эфиром Π°Ρ†Π΅Ρ‚ΠΈΠ»Π΅Π½Π΄ΠΈΠΊΠ°Ρ€Π±ΠΎΠ½ΠΎΠ²ΠΎΠΉ кислоты Π² Π°Π±ΡΠΎΠ»ΡŽΡ‚Π½ΠΎΠΌ кипящСм этанолС ΠΏΡ€ΠΈΠ²ΠΎΠ΄ΠΈΡ‚ ΠΊ ΠΎΠ±Ρ€Π°Π·ΠΎΠ²Π°Π½ΠΈΡŽ этил 7-оксо-[1,3,4]Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»[3,2-Π°]ΠΏΠΈΡ€ΠΈΠΌΠΈΠ΄ΠΈΠ½-5-карбоксилатов. Π Π΅Π·ΡƒΠ»ΡŒΡ‚Π°Ρ‚Ρ‹ изучСния ΠΏΡ€ΠΎΡ‚ΠΈΠ²ΠΎΠΌΠΈΠΊΡ€ΠΎΠ±Π½Ρ‹Ρ… свойств 2-Π°ΠΌΠΈΠ½ΠΎ-1,3,4-Ρ‚ΠΈΠ°Π΄ΠΈΠ°Π·ΠΎΠ»ΠΎΠ² ΠΏΠΎΠΊΠ°Π·Π°Π»ΠΈ, Ρ‡Ρ‚ΠΎ синтСзированныС соСдинСния ΠΎΠ±Π»Π°Π΄Π°ΡŽΡ‚ ΡƒΠΌΠ΅Ρ€Π΅Π½Π½ΠΎΠΉ Π±Π°ΠΊΡ‚Π΅Ρ€ΠΈΡ†ΠΈΠ΄Π½ΠΎΠΉ ΠΈ Ρ„ΡƒΠ½Π³ΠΈΡ†ΠΈΠ΄Π½ΠΎΠΉ Π°ΠΊΡ‚ΠΈΠ²Π½ΠΎΡΡ‚ΡŒΡŽ.ДослідТСння присвячСнС синтСзу Π½ΠΎΠ²ΠΈΡ… прСдставників 2-Π°ΠΌΡ–Π½ΠΎ-5-Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π»-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»ΡŒΠ½ΠΈΡ… систСм, Π²ΠΈΠ²Ρ‡Π΅Π½Π½ΡŽ дСяких Ρ—Ρ… Ρ…Ρ–ΠΌΡ–Ρ‡Π½ΠΈΡ… ΠΏΠ΅Ρ€Π΅Ρ‚Π²ΠΎΡ€Π΅Π½ΡŒ Ρ‚Π° Π±Π°ΠΊΡ‚Π΅Ρ€ΠΈΡ†ΠΈΠ΄Π½ΠΎΡ— активності. Показано, Ρ‰ΠΎ тіосСмікарбазони, ΠΎΡ‚Ρ€ΠΈΠΌΠ°Π½Ρ– ΠΊΠΎΠ½Π΄Π΅Π½ΡΠ°Ρ†Ρ–Ρ”ΡŽ 4-Ρ…Π»ΠΎΡ€ΠΎ-1Н-5-Ρ„ΠΎΡ€ΠΌΡ–Π»Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² Ρ–Π· тіосСмікарбазидом, ΠΏΡ€ΠΈ Π½Π°Π³Ρ€Ρ–Π²Π°Π½Π½Ρ– Π· 3-ΠΊΡ€Π°Ρ‚Π½ΠΈΠΌ надлишком гСксагідрату Ρ…Π»ΠΎΡ€ΠΈΠ΄Ρƒ Π·Π°Π»Ρ–Π·Π°(Π†Π†Π†) Ρƒ 80%-Π½Ρ–ΠΉ ΠΎΡ†Ρ‚ΠΎΠ²Ρ–ΠΉ кислоті Π·Π°Π·Π½Π°ΡŽΡ‚ΡŒ ΠΎΠΊΠΈΡΠ½ΡŽΠ²Π°Π»ΡŒΠ½ΠΎΡ— Ρ†ΠΈΠΊΠ»Ρ–Π·Π°Ρ†Ρ–Ρ— Π· утворСнням Π½ΠΎΠ²ΠΈΡ… 2-Π°ΠΌΡ–Π½ΠΎ-5-(4-Ρ…Π»ΠΎΡ€ΠΎΡ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»-5-Ρ–Π»)-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»Ρ–Π². Π‘ΠΈΠ½Ρ‚Π΅Π·ΠΎΠ²Π°Π½Ρ– сполуки Π²Ρ–Π΄Π½ΠΎΡΡΡ‚ΡŒΡΡ Π΄ΠΎ Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ†ΠΈΠΊΠ»Ρ–Ρ‡Π½ΠΈΡ… систСм Π· Π΄Π²ΠΎΠΌΠ° Π΅Π»Π΅ΠΊΡ‚Ρ€ΠΎΡ„Ρ–Π»ΡŒΠ½ΠΈΠΌΠΈ Ρ†Π΅Π½Ρ‚Ρ€Π°ΠΌΠΈ, Ρ‰ΠΎ часто Π²ΠΈΠΊΠΎΡ€ΠΈΡΡ‚ΠΎΠ²ΡƒΡ”Ρ‚ΡŒΡΡ ΠΏΡ€ΠΈ ΠΎΡ‚Ρ€ΠΈΠΌΠ°Π½Π½Ρ– Π±Ρ–Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ†ΠΈΠΊΠ»Ρ–Ρ‡Π½ΠΈΡ… Π±Ρ–ΠΎΠ»ΠΎΠ³Ρ–Ρ‡Π½ΠΎ Π°ΠΊΡ‚ΠΈΠ²Π½ΠΈΡ… систСм. ΠŸΡ€ΠΈ Π²ΠΈΠ²Ρ‡Π΅Π½Π½Ρ– Ρ…Ρ–ΠΌΡ–Ρ‡Π½ΠΎΡ— ΠΏΠΎΠ²Π΅Π΄Ρ–Π½ΠΊΠΈ дослідТуваних 2-Π°ΠΌΡ–Π½ΠΎ-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»Ρ–Π² Ρƒ рСакціях анСлювання Π· низкою Π±Ρ–Π΅Π»Π΅ΠΊΡ‚Ρ€ΠΎΡ„Ρ–Π»ΡŒΠ½ΠΈΡ… Ρ€Π΅Π°Π³Π΅Π½Ρ‚Ρ–Π² виявлСно, Ρ‰ΠΎ Π²ΠΎΠ½ΠΈ Π½Π΅ Ρ€Π΅Π°Π³ΡƒΡŽΡ‚ΡŒ Π½Ρ– Π· Ρ„Π΅Π½Π°Ρ†ΠΈΠ»Π±Ρ€ΠΎΠΌΡ–Π΄ΠΎΠΌ, Π½Ρ– Π· ΠΌΠ°Π»ΠΎΠ½ΠΎΠ½Ρ–Ρ‚Ρ€ΠΈΠ»ΠΎΠΌ, Π° Π· Ρ…Π»ΠΎΡ€ΠΎΠ°Ρ†Π΅Ρ‚ΠΈΠ»Ρ…Π»ΠΎΡ€ΠΈΠ΄ΠΎΠΌ ΡƒΡ‚Π²ΠΎΡ€ΡŽΡ”Ρ‚ΡŒΡΡ ΠΏΡ€ΠΎΠ΄ΡƒΠΊΡ‚ 5-Π°ΠΌΡ–Π½ΠΎΠ°Ρ†ΠΈΠ»ΡŽΠ²Π°Π½Π½Ρ, який Π½Π°Π²Ρ–Ρ‚ΡŒ ΠΏΡ€ΠΈ Π½Π°Π³Ρ€Ρ–Π²Π°Π½Π½Ρ– Π² киплячому Π”ΠœΠ€Π Π² присутності K2CO3 Π½Π΅ ΡΡ…ΠΈΠ»ΡŒΠ½ΠΈΠΉ Π΄ΠΎ Π²Π½ΡƒΡ‚Ρ€Ρ–ΡˆΠ½ΡŒΠΎΠΌΠΎΠ»Π΅ΠΊΡƒΠ»ΡΡ€Π½ΠΎΡ— циклокондСнсації. Π’ Ρ‚ΠΎΠΉ ΠΆΠ΅ час нагрівання 2-Π°ΠΌΡ–Π½ΠΎ-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»Ρ–Π² Π· Π΄Ρ–Π΅Ρ‚ΠΈΠ»ΠΎΠ²ΠΈΠΌ Π΅Ρ„Ρ–Ρ€ΠΎΠΌ Π°Ρ†Π΅Ρ‚ΠΈΠ»Π΅Π½Π΄ΠΈΠΊΠ°Ρ€Π±ΠΎΠ½ΠΎΠ²ΠΎΡ— кислоти Π² Π°Π±ΡΠΎΠ»ΡŽΡ‚Π½ΠΎΠΌΡƒ киплячому Π΅Ρ‚Π°Π½ΠΎΠ»Ρ– ΠΏΡ€ΠΈΠ²ΠΎΠ΄ΠΈΡ‚ΡŒ Π΄ΠΎ утворСння Π΅Ρ‚ΠΈΠ» 7-оксо-[1,3,4]Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»ΠΎ[3,2-Π°]ΠΏΡ–Ρ€ΠΈΠΌΡ–Π΄ΠΈΠ½-5-карбоксилатів. Π Π΅Π·ΡƒΠ»ΡŒΡ‚Π°Ρ‚ΠΈ вивчСння Π°Π½Ρ‚ΠΈΠΌΡ–ΠΊΡ€ΠΎΠ±Π½ΠΈΡ… властивостСй 2-Π°ΠΌΡ–Π½ΠΎ-1,3,4-Ρ‚Ρ–Π°Π΄Ρ–Π°Π·ΠΎΠ»Ρ–Π² ΠΏΠΎΠΊΠ°Π·Π°Π»ΠΈ, Ρ‰ΠΎ синтСзовані сполуки Π²ΠΈΡΠ²Π»ΡΡŽΡ‚ΡŒ ΠΏΠΎΠΌΡ–Ρ€Π½Ρƒ Π±Π°ΠΊΡ‚Π΅Ρ€ΠΈΡ†ΠΈΠ΄Π½Ρƒ Ρ‚Π° Ρ„ΡƒΠ½Π³Ρ–Ρ†ΠΈΠ΄Π½Ρƒ Π΄Ρ–ΡŽ

    АлкСнілімідазоли: ΠΌΠ΅Ρ‚ΠΎΠ΄ΠΈ синтСзу Ρ‚Π° Ρ…Ρ–ΠΌΡ–Ρ‡Π½Ρ– властивості

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    The aim of this review was to summarize and systematize literature on chemistry of alkenylsubstituted imidazoles known as important synthetic substrates and precursors for the synthesis of biologically active substances. Two approaches to the synthesis of these compounds are reviewed: 1) the imidazole ring formation based on functionalized alkenyl compounds; 2) functionalization of imidazole derivatives with the alkenyl moiety. The second approach prevails and includes condensation of methylimidazoles with carbonyl compounds, reactions of formylimidazoles with compounds containing activated methylene groups and phosphorus ylides, as well as reactions of dehydration and dehydrohalogenation of substituted imidazoles. The methods of synthesis of alkenylsubstituted imidazoles have been analyzed in detail; their synthetic potential and limits have been described. Special attention is paid to the authors’ own research on the synthesis of new 4-chloro-5-alkenylsubstituted imidazoles using 5-formylimidazoles as precursors. Analysis of the chemical properties of alkenylsubstituted imidazoles has allowed conducting their strict classification and systematizing their typical transformations. Reactions of cyclocondensation are the first ones to be mentioned, they proceed through the interaction of the alkenyl moiety with another functional group or endocyclic Nitrogen. Other transformations such as heterocyclofunctionalization, oxidation and reduction are based on transformation of the alkenyl moiety. It should be noted that heterocyclization processes are new for chemistry of alkenylimidazoles, they are successfully applied to 5-(2-nitro-alkenyl)- and 5-(2-arylvinyl)substituted derivatives, and due to them it is possible to obtain new promising hybrid structures.Π’ ΠΎΠ±Π·ΠΎΡ€Π½ΠΎΠΉ ΡΡ‚Π°Ρ‚ΡŒΠ΅ Π²ΠΏΠ΅Ρ€Π²Ρ‹Π΅ систСматизированы ΠΈ ΠΎΠ±ΠΎΠ±Ρ‰Π΅Π½Ρ‹ Π»ΠΈΡ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½Ρ‹Π΅ источники, ΠΊΠ°ΡΠ°ΡŽΡ‰ΠΈΠ΅ΡΡ химия всСх Ρ‚ΠΈΠΏΠΎΠ² Π°Π»ΠΊΠ΅Π½ΠΈΠ»Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² ΠΊΠ°ΠΊ Π²Π°ΠΆΠ½Ρ‹Ρ… синтСтичСских субстратов ΠΈ ΠΏΡ€Π΅Π΄ΡˆΠ΅ΡΡ‚Π²Π΅Π½Π½ΠΈΠΊΠΎΠ² для конструирования биологичСски Π°ΠΊΡ‚ΠΈΠ²Π½Ρ‹Ρ… вСщСств. ΠŸΠΎΠ΄Ρ€ΠΎΠ±Π½ΠΎ рассмотрСны Π΄Π²Π° ΠΏΠΎΠ΄Ρ…ΠΎΠ΄Π° ΠΊ ΠΈΡ… синтСзу : 1) Ρ„ΠΎΡ€ΠΌΠΈΡ€ΠΎΠ²Π°Π½ΠΈΠ΅ имидазольного ядра Π½Π° основС Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΡŒΠ½Ρ‹Ρ… Π°Π»ΠΊΠ΅Π½ΠΈΠ»ΡŒΠ½Ρ‹Ρ… соСдинСний; 2) алкСнилфункционализация Ρ€Π°Π·Π½ΠΎΠΎΠ±Ρ€Π°Π·Π½Ρ‹Ρ… ΠΏΡ€ΠΎΠΈΠ·Π²ΠΎΠ΄Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»Π°. Π’Ρ‚ΠΎΡ€ΠΎΠΉ Π²Π°Ρ€ΠΈΠ°Π½Ρ‚ являСтся Π΄ΠΎΠΌΠΈΠ½ΠΈΡ€ΡƒΡŽΡ‰ΠΈΠΌ ΠΈ Π²ΠΊΠ»ΡŽΡ‡Π°Π΅Ρ‚ Π² сСбя кондСнсации ΠΌΠ΅Ρ‚ΠΈΠ»ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² с ΠΊΠ°Ρ€Π±ΠΎΠ½ΠΈΠ»ΡŒΠ½Ρ‹ΠΌΠΈ соСдинСниями, Ρ€Π΅Π°ΠΊΡ†ΠΈΠΈ Ρ„ΠΎΡ€ΠΌΠΈΠ»ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² с ΠΌΠ΅Ρ‚ΠΈΠ»Π΅Π½Π°ΠΊΡ‚ΠΈΠ²Π½Ρ‹ΠΌΠΈ Ρ€Π΅Π°Π³Π΅Π½Ρ‚Π°ΠΌΠΈ ΠΈΠ»ΠΈΠ΄Π°ΠΌΠΈ фосфора, Π° Ρ‚Π°ΠΊΠΆΠ΅ Ρ€Π΅Π°ΠΊΡ†ΠΈΠΈ Π΄Π΅Π³ΠΈΠ΄Ρ€Π°Ρ‚Π°Ρ†ΠΈΠΈ ΠΈ дСгидрогСнирования Π·Π°ΠΌΠ΅Ρ‰Π΅Π½Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ². Π”Π΅Ρ‚Π°Π»ΡŒΠ½ΠΎ ΠΏΡ€ΠΎΠ°Π½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Ρ‹ ΠΌΠ΅Ρ‚ΠΎΠ΄Ρ‹ получСния Π°Π»ΠΊΠ΅Π½ΠΈΠ»Π·Π°ΠΌΠ΅Ρ‰Π΅Π½Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ², ΠΎΡ‡Π΅Ρ€Ρ‡Π΅Π½Ρ‹ ΠΈΡ… ΠΏΡ€Π΅ΠΏΠ°Ρ€Π°Ρ‚ΠΈΠ²Π½Ρ‹Π΅ Π³Ρ€Π°Π½ΠΈΡ†Ρ‹ ΠΈ раскрыт синтСтичСский ΠΏΠΎΡ‚Π΅Π½Ρ†ΠΈΠ°Π». ОсобоС Π²Π½ΠΈΠΌΠ°Π½ΠΈΠ΅ ΡƒΠ΄Π΅Π»Π΅Π½ΠΎ собствСнным исслСдованиям Π°Π²Ρ‚ΠΎΡ€ΠΎΠ² ΠΏΠΎ ΠΏΠΎΠ»ΡƒΡ‡Π΅Π½ΠΈΡŽ Π½ΠΎΠ²Ρ‹Ρ… Ρ‚ΠΈΠΏΠΎΠ² 4-Ρ…Π»ΠΎΡ€-5-Π°Π»ΠΊΠ΅Π½ΠΈΠ»Π·Π°ΠΌΠ΅Ρ‰Π΅Π½Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² Π½Π° основС ΡΠΎΠΎΡ‚Π²Π΅Ρ‚ΡΡ‚Π²ΡƒΡŽΡ‰ΠΈΡ… 5-Ρ„ΠΎΡ€ΠΌΠΈΠ»ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ². Анализ химичСских свойств Π°Π»ΠΊΠ΅Π½ΠΈΠ»Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹Ρ… ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ² ΠΏΠΎΠ·Π²ΠΎΠ»ΠΈΠ» провСсти ΠΈΡ… ΡΡ‚Ρ€ΠΎΠ³ΡƒΡŽ ΠΊΠ»Π°ΡΡΠΈΡ„ΠΈΠΊΠ°Ρ†ΠΈΡŽ ΠΈ ΡΠΈΡΡ‚Π΅ΠΌΠ°Ρ‚ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Ρ‚ΡŒ Π½Π°ΠΈΠ±ΠΎΠ»Π΅Π΅ Ρ‚ΠΈΠΏΠΈΡ‡Π½Ρ‹Π΅ прСвращСния. К Π½ΠΈΠΌ, Π² ΠΏΠ΅Ρ€Π²ΡƒΡŽ ΠΎΡ‡Π΅Ρ€Π΅Π΄ΡŒ, слСдуСт отнСсти Ρ€Π΅Π°ΠΊΡ†ΠΈΠΈ циклокондСнсации, ΠΊΠΎΡ‚ΠΎΡ€Ρ‹Π΅ ΠΎΠ±Ρ‹Ρ‡Π½ΠΎ Ρ€Π΅Π°Π»ΠΈΠ·ΡƒΡŽΡ‚ΡΡ с участиСм алкСнильного Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚Π° ΠΈ ΠΈΠ½ΠΎΠ³ΠΎ Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΡŒΠ½ΠΎΠ³ΠΎ замСститСля ΠΈΠ»ΠΈ Π°Ρ‚ΠΎΠΌΠ° Π°Π·ΠΎΡ‚Π° Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ†ΠΈΠΊΠ»Π°. НС ΠΌΠ΅Π½Π΅Π΅ Π·Π½Π°Ρ‡ΠΈΠΌΡ‹ΠΌΠΈ ΡΠ²Π»ΡΡŽΡ‚ΡΡ Ρ€Π°Π·Π½ΠΎΠΎΠ±Ρ€Π°Π·Π½Ρ‹Π΅ прСвращСния алкСнильного замСститСля: гСтСроциклофункционализация, окислСниС ΠΈ восстановлСниС. ЦСлСсообразно ΠΎΡ‚ΠΌΠ΅Ρ‚ΠΈΡ‚ΡŒ, Ρ‡Ρ‚ΠΎ процСссы Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΠΈΠ·Π°Ρ†ΠΈΠΈ ΡΠ²Π»ΡΡŽΡ‚ΡΡ Π½ΠΎΠ²Ρ‹ΠΌΠΈ Π² Ρ…ΠΈΠΌΠΈΠΈ Π°Π»ΠΊΠ΅Π½ΠΈΠ»ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»ΠΎΠ², ΡƒΠ΄Π°Ρ‡Π½ΠΎ раскрыты Π½Π° ΠΏΡ€ΠΈΠΌΠ΅Ρ€Π°Ρ… ΠΈΡ… 5-(2-Π½ΠΈΡ‚Ρ€ΠΎΠ°Π»ΠΊΠ΅Π½ΠΈΠ»)- ΠΈ 5-(2-Π°Ρ€ΠΎΠΈΠ»Π²ΠΈΠ½ΠΈΠ»)Π·Π°ΠΌΠ΅Ρ‰Π΅Π½Π½Ρ‹Ρ… прСдставитСлСй ΠΈ Π΄Π°ΡŽΡ‚ Π²ΠΎΠ·ΠΌΠΎΠΆΠ½ΠΎΡΡ‚ΡŒ ΠΏΠΎΠ»ΡƒΡ‡Π°Ρ‚ΡŒ Π½ΠΎΠ²Ρ‹Π΅ биопСрспСктивныС Π³ΠΈΠ±Ρ€ΠΈΠ΄Π½Ρ‹Π΅ структуры.Β Π’ оглядовій статті Π²ΠΏΠ΅Ρ€ΡˆΠ΅ систСматизовані Ρ‚Π° ΡƒΠ·Π°Π³Π°Π»ΡŒΠ½Π΅Π½Ρ– Π»Ρ–Ρ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½Ρ– Π΄ΠΆΠ΅Ρ€Π΅Π»Π°, які ΡΡ‚ΠΎΡΡƒΡŽΡ‚ΡŒΡΡ Ρ…Ρ–ΠΌΡ–Ρ— всіх Ρ‚ΠΈΠΏΡ–Π² Π°Π»ΠΊΠ΅Π½Ρ–Π»Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² як Π²Π°ΠΆΠ»ΠΈΠ²ΠΈΡ… синтСтичних субстратів Ρ‚Π° ΠΏΠΎΠΏΠ΅Ρ€Π΅Π΄Π½ΠΈΠΊΡ–Π² для ΠΊΠΎΠ½ΡΡ‚Ρ€ΡƒΡŽΠ²Π°Π½Π½Ρ Π±Ρ–ΠΎΠ»ΠΎΠ³Ρ–Ρ‡Π½ΠΎ Π°ΠΊΡ‚ΠΈΠ²Π½ΠΈΡ… Ρ€Π΅Ρ‡ΠΎΠ²ΠΈΠ½. Π”Π΅Ρ‚Π°Π»ΡŒΠ½ΠΎ розглянуті Π΄Π²Π° ΠΏΡ–Π΄Ρ…ΠΎΠ΄ΠΈ Π΄ΠΎ Ρ—Ρ… синтСзу: 1) формування Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»ΡŒΠ½ΠΎΠ³ΠΎ ядра Π½Π° Π±Π°Π·Ρ– Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»ΡŒΠ½ΠΈΡ… Π°Π»ΠΊΠ΅Π½Ρ–Π»ΡŒΠ½ΠΈΡ… сполук; 2) алкСнілфункціоналізація Ρ€Ρ–Π·Π½ΠΎΠΌΠ°Π½Ρ–Ρ‚Π½ΠΈΡ… ΠΏΠΎΡ…Ρ–Π΄Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρƒ. Π”Ρ€ΡƒΠ³ΠΈΠΉ Π²Π°Ρ€Ρ–Π°Π½Ρ‚ Ρ” Π΄ΠΎΠΌΡ–Π½ΡƒΡŽΡ‡ΠΈΠΌ Ρ– Π²ΠΊΠ»ΡŽΡ‡Π°Ρ” Π² сСбС кондСнсації ΠΌΠ΅Ρ‚ΠΈΠ»Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² Ρ–Π· ΠΊΠ°Ρ€Π±ΠΎΠ½Ρ–Π»ΡŒΠ½ΠΈΠΌΠΈ сполуками, Ρ€Π΅Π°ΠΊΡ†Ρ–Ρ— Ρ„ΠΎΡ€ΠΌΡ–Π»Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² Ρ–Π· ΠΌΠ΅Ρ‚ΠΈΠ»Π΅Π½Π°ΠΊΡ‚ΠΈΠ²Π½ΠΈΠΌΠΈ Ρ€Π΅Π°Π³Π΅Π½Ρ‚Π°ΠΌΠΈ Ρ‚Π° Ρ–Π»Ρ–Π΄Π°ΠΌΠΈ фосфору, Π° Ρ‚Π°ΠΊΠΎΠΆ Ρ€Π΅Π°ΠΊΡ†Ρ–Ρ— Π΄Π΅Π³Ρ–Π΄Ρ€Π°Ρ‚Π°Ρ†Ρ–Ρ— Ρ‚Π° дСгідрогалогСнування Π·Π°ΠΌΡ–Ρ‰Π΅Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π². Π”Π΅Ρ‚Π°Π»ΡŒΠ½ΠΎ ΠΏΡ€ΠΎΠ°Π½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½Ρ– ΠΌΠ΅Ρ‚ΠΎΠ΄ΠΈ одСрТання Π°Π»ΠΊΠ΅Π½Ρ–Π»Π·Π°ΠΌΡ–Ρ‰Π΅Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π², окрСслСні Ρ—Ρ… ΠΏΡ€Π΅ΠΏΠ°Ρ€Π°Ρ‚ΠΈΠ²Π½Ρ– ΠΌΠ΅ΠΆΡ– Ρ‚Π° Ρ€ΠΎΠ·ΠΊΡ€ΠΈΡ‚ΠΎ синтСтичний ΠΏΠΎΡ‚Π΅Π½Ρ†Ρ–Π°Π». Особлива ΡƒΠ²Π°Π³Π° ΠΏΡ€ΠΈΠ΄Ρ–Π»Π΅Π½Π° власним дослідТСнням Π°Π²Ρ‚ΠΎΡ€Ρ–Π² Π· отримання Π½ΠΎΠ²ΠΈΡ… Ρ‚ΠΈΠΏΡ–Π² 4-Ρ…Π»ΠΎΡ€ΠΎ-5-Π°Π»ΠΊΠ΅Π½Ρ–Π»Π·Π°ΠΌΡ–Ρ‰Π΅Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² Π½Π° основі Π²Ρ–Π΄ΠΏΠΎΠ²Ρ–Π΄Π½ΠΈΡ… 5-Ρ„ΠΎΡ€ΠΌΡ–Π»Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π². Аналіз Ρ…Ρ–ΠΌΡ–Ρ‡Π½ΠΈΡ… властивостСй Π°Π»ΠΊΠ΅Π½Ρ–Π»Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½ΠΈΡ… Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π² Π΄ΠΎΠ·Π²ΠΎΠ»ΠΈΠ² провСсти Ρ—Ρ… строгу ΠΊΠ»Π°ΡΠΈΡ„Ρ–ΠΊΠ°Ρ†Ρ–ΡŽ Ρ‚Π° систСматизувати Π½Π°ΠΉΡ‚ΠΈΠΏΠΎΠ²Ρ–ΡˆΡ– пСрСтворСння. Π”ΠΎ Π½ΠΈΡ…, Ρƒ ΠΏΠ΅Ρ€ΡˆΡƒ Ρ‡Π΅Ρ€Π³Ρƒ, Π²Π°Ρ€Ρ‚ΠΎ віднСсти Ρ€Π΅Π°ΠΊΡ†Ρ–Ρ— циклокондСнсації, які Π·Π°Π·Π²ΠΈΡ‡Π°ΠΉ Ρ€Π΅Π°Π»Ρ–Π·ΡƒΡŽΡ‚ΡŒΡΡ Π·Π° ΡƒΡ‡Π°ΡΡ‚ΡŽ Π°Π»ΠΊΠ΅Π½Ρ–Π»ΡŒΠ½ΠΎΠ³ΠΎ Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚Π° Ρ‚Π° Ρ–Π½ΡˆΠΎΠ³ΠΎ Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»ΡŒΠ½ΠΎΠ³ΠΎ замісника Π°Π±ΠΎ Π°Ρ‚ΠΎΠΌΠ° Π°Π·ΠΎΡ‚Ρƒ Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ†ΠΈΠΊΠ»Ρƒ. НС мСнш Π·Π½Π°Ρ‡ΠΈΠΌΠΈΠΌΠΈ Ρ” Ρ€Ρ–Π·Π½ΠΎΠΌΠ°Π½Ρ–Ρ‚Π½Ρ– пСрСтворСння Π°Π»ΠΊΠ΅Π½Ρ–Π»ΡŒΠ½ΠΎΠ³ΠΎ замісника: гСтСроциклофункціоналізація, окиснСння Ρ‚Π° відновлСння. Π”ΠΎΡ€Π΅Ρ‡Π½ΠΎ Π²Ρ–Π΄Π·Π½Π°Ρ‡ΠΈΡ‚ΠΈ, Ρ‰ΠΎ процСси Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ†ΠΈΠΊΠ»ΠΎΡ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»Ρ–Π·Π°Ρ†Ρ–Ρ— Ρ” Π½ΠΎΠ²ΠΈΠΌΠΈ Π² Ρ…Ρ–ΠΌΡ–Ρ— Π°Π»ΠΊΠ΅Π½Ρ–Π»Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π², Π²Π΄Π°Π»ΠΎ Ρ€ΠΎΠ·ΠΊΡ€ΠΈΡ‚Ρ– Π½Π° ΠΏΡ€ΠΈΠΊΠ»Π°Π΄Π°Ρ… Ρ—Ρ… 5-(2-Π½Ρ–Ρ‚Ρ€ΠΎΠ°Π»ΠΊΠ΅Π½Ρ–Π»)- Ρ‚Π° 5-(2-Π°Ρ€ΠΎΡ—Π»Π²Ρ–Π½Ρ–Π»)Π·Π°ΠΌΡ–Ρ‰Π΅Π½ΠΈΡ… прСдставників Ρ– Π΄Π°ΡŽΡ‚ΡŒ Π·ΠΌΠΎΠ³Ρƒ ΠΎΡ‚Ρ€ΠΈΠΌΡƒΠ²Π°Ρ‚ΠΈ Π½ΠΎΠ²Ρ– біопСрспСктивні Π³Ρ–Π±Ρ€ΠΈΠ΄Π½Ρ– структури.

    CΠΈΠ½Ρ‚Π΅Π· Ρ‚Π° Π±Ρ–ΠΎΠ»ΠΎΠ³Ρ–Ρ‡Π½Π° Π°ΠΊΡ‚ΠΈΠ²Π½Ρ–ΡΡ‚ΡŒ Π°Π·ΠΎΠ»Ρ–Π»Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΡ… кислот

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    oai:ojs.journals.uran.ua:article/88983The review systematizes the published data concerning the methods of synthesis of azoles (imidazoles, oxazoles, thiazoles, pyrazoles, triazoles, and tetrazoles) functionalized by the carboxymethyl thiol fragment; the results of studies of the biological activity of this class of compounds have been also analysed. Today the main directions for the synthesis of azolylthioacetic acids and their derivatives are reactions of azoles that contain the thiol group with haloacetic acids and their derivatives, and the nucleophilic substitution of halogen in the haloazoles under the action of thioglycolic acid. Moreover, the addition of thioles to multiple bonds, activated with electron withdrawing groups has found its application together with formation of the azole cycle from heterofunctional systems that already contain the component of thioacetic acid. To obtain polyfunctional derivatives of azolylthioacetic acids the modification of azole functional groups that already contain the fragment of thioacetic acid is sometimes used. The summary of the published data gives strong reasons to assert that the derivatives of azolylthioacetic acids are characterized by diverse biological effects. For instance, they are characterized by the antioxidant, hypoglycemic, antitubercular, analgesic, antiviral, antimicrobial, and antifungal activity. The material analysed indicates that the search for new bioactive compounds among the azolylthioacetic acids is very promising.Π’ ΠΎΠ±Π·ΠΎΡ€Π΅ систСматизированы Π»ΠΈΡ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½Ρ‹Π΅ Π΄Π°Π½Π½Ρ‹Π΅ ΠΏΠΎ ΠΌΠ΅Ρ‚ΠΎΠ΄Π°ΠΌ синтСза Π°Π·ΠΎΠ»ΠΎΠ² (ΠΈΠΌΠΈΠ΄Π°Π·ΠΎΠ»Π°, оксазола, Ρ‚ΠΈΠ°Π·ΠΎΠ»Π°, ΠΏΠΈΡ€Π°Π·ΠΎΠ»Π°, Ρ‚Ρ€ΠΈΠ°Π·ΠΎΠ»ΠΎΠ² ΠΈ Ρ‚Π΅Ρ‚Ρ€Π°Π·ΠΎΠ»Π°), Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹Ρ… ΠΊΠ°Ρ€Π±ΠΎΠΊΡΠΈΠΌΠ΅Ρ‚ΠΈΠ»Ρ‚ΠΈΠΎΠ»ΡŒΠ½Ρ‹ΠΌ Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ΠΎΠΌ, Π° Ρ‚Π°ΠΊΠΆΠ΅ ΠΏΡ€ΠΎΠ°Π½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Ρ‹ Ρ€Π΅Π·ΡƒΠ»ΡŒΡ‚Π°Ρ‚Ρ‹ изучСния биологичСской активности Π΄Π°Π½Π½ΠΎΠ³ΠΎ класса соСдинСний. ΠžΡΠ½ΠΎΠ²Π½Ρ‹ΠΌΠΈ направлСниями синтСза азолилтиоуксусных кислот ΠΈ ΠΈΡ… ΠΏΡ€ΠΎΠΈΠ·Π²ΠΎΠ΄Π½Ρ‹Ρ… Π½Π° сСгодня ΡΠ²Π»ΡΡŽΡ‚ΡΡ Ρ€Π΅Π°ΠΊΡ†ΠΈΠΈ Π°Π·ΠΎΠ»ΠΎΠ², содСрТащих Ρ‚ΠΈΠΎΠ»ΡŒΠ½ΡƒΡŽ Π³Ρ€ΡƒΠΏΠΏΡƒ, с галогСнуксусными кислотами ΠΈ ΠΈΡ… ΠΏΡ€ΠΎΠΈΠ·Π²ΠΎΠ΄Π½Ρ‹ΠΌΠΈ, Π½ΡƒΠΊΠ»Π΅ΠΎΡ„ΠΈΠ»ΡŒΠ½ΠΎΠ΅ Π·Π°ΠΌΠ΅Ρ‰Π΅Π½ΠΈΠ΅ Π³Π°Π»ΠΎΠ³Π΅Π½Π° Π² Π³Π°Π»ΠΎΠ³Π΅Π½Π°Π·ΠΎΠ»Π°Ρ… ΠΏΡ€ΠΈ воздСйствии Ρ‚ΠΈΠΎΠ³Π»ΠΈΠΊΠΎΠ»Π΅Π²ΠΎΠΉ кислоты. ΠšΡ€ΠΎΠΌΠ΅ Ρ‚ΠΎΠ³ΠΎ, нашли ΠΏΡ€ΠΈΠΌΠ΅Π½Π΅Π½ΠΈΠ΅ присоСдинСния Ρ‚ΠΈΠΎΠ»ΠΎΠ² ΠΊ ΠΊΡ€Π°Ρ‚Π½Ρ‹ΠΌ связям, Π°ΠΊΡ‚ΠΈΠ²ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹ΠΌ элСктроноакцСпторными Π³Ρ€ΡƒΠΏΠΏΠΈΡ€ΠΎΠ²ΠΊΠ°ΠΌΠΈ, Π° Ρ‚Π°ΠΊΠΆΠ΅ формирования азольного Ρ†ΠΈΠΊΠ»Π° с Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΡŒΠ½Ρ‹ΠΌΠΈ систСмами, ΠΊΠΎΡ‚ΠΎΡ€Ρ‹Π΅ ΡƒΠΆΠ΅ содСрТат Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ тиоуксусной кислоты. Для получСния ΠΏΠΎΠ»ΠΈΡ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΡŒΠ½Ρ‹Ρ… ΠΏΡ€ΠΎΠΈΠ·Π²ΠΎΠ΄Π½Ρ‹Ρ… азолилтиоуксусных кислот ΠΈΠ½ΠΎΠ³Π΄Π° ΠΈΡΠΏΠΎΠ»ΡŒΠ·ΡƒΠ΅Ρ‚ΡΡ Π²Π°Ρ€ΠΈΠ°Π½Ρ‚ ΠΌΠΎΠ΄ΠΈΡ„ΠΈΠΊΠ°Ρ†ΠΈΠΈ Ρ„ΡƒΠ½ΠΊΡ†ΠΈΠΎΠ½Π°Π»ΡŒΠ½Ρ‹Ρ… Π³Ρ€ΡƒΠΏΠΏ Π°Π·ΠΎΠ»ΠΎΠ² с ΡƒΠΆΠ΅ ΠΈΠΌΠ΅ΡŽΡ‰ΠΈΠΌΡΡ Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ΠΎΠΌ тиоуксусной кислоты. ΠžΠ±ΠΎΠ±Ρ‰Π΅Π½ΠΈΠ΅ Π»ΠΈΡ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½Ρ‹Ρ… Π΄Π°Π½Π½Ρ‹Ρ… Π΄Π°Π΅Ρ‚ всС основания ΡƒΡ‚Π²Π΅Ρ€ΠΆΠ΄Π°Ρ‚ΡŒ, Ρ‡Ρ‚ΠΎ ΠΏΡ€ΠΎΠΈΠ·Π²ΠΎΠ΄Π½Ρ‹ΠΌ азолилтиоуксусных кислот свойствСнно Ρ€Π°Π·Π½ΠΎΠΏΠ»Π°Π½ΠΎΠ²ΠΎΠ΅ биологичСскоС дСйствиС. Π’ частности, для Π½ΠΈΡ… Ρ…Π°Ρ€Π°ΠΊΡ‚Π΅Ρ€Π½Π° антиоксидантная, гипогликСмичСская, противотубСркулСзная, Π°Π½Π°Π»ΡŒΠ³Π΅Ρ‚ΠΈΡ‡Π΅ΡΠΊΠ°Ρ, противовирусная, противомикробная ΠΈ противогрибковая Π°ΠΊΡ‚ΠΈΠ²Π½ΠΎΡΡ‚ΡŒ. ΠŸΡ€ΠΎΠ°Π½Π°Π»ΠΈΠ·ΠΈΡ€ΠΎΠ²Π°Π½Π½Ρ‹ΠΉ ΠΌΠ°Ρ‚Π΅Ρ€ΠΈΠ°Π» ΡΠ²ΠΈΠ΄Π΅Ρ‚Π΅Π»ΡŒΡΡ‚Π²ΡƒΠ΅Ρ‚ ΠΎ пСрспСктивности поиска Π½ΠΎΠ²Ρ‹Ρ… Π±ΠΈΠΎΠ°ΠΊΡ‚ΠΈΠ²Π½Ρ‹Ρ… вСщСств Π² ряду азолилтиоуксусных кислот.Π’ огляді систСматизовані Π»Ρ–Ρ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½Ρ– Π΄Π°Π½Ρ– Ρ‰ΠΎΠ΄ΠΎ ΠΌΠ΅Ρ‚ΠΎΠ΄Ρ–Π² синтСзу Π°Π·ΠΎΠ»Ρ–Π² (Ρ–ΠΌΡ–Π΄Π°Π·ΠΎΠ»Ρ–Π², оксазолів, Ρ‚Ρ–Π°Π·ΠΎΠ»Ρ–Π², ΠΏΡ–Ρ€Π°Π·ΠΎΠ»Ρ–Π², Ρ‚Ρ€ΠΈΠ°Π·ΠΎΠ»Ρ–Π² Ρ‚Π° Ρ‚Π΅Ρ‚Ρ€Π°Π·ΠΎΠ»Ρ–Π²), Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½ΠΈΡ… ΠΊΠ°Ρ€Π±ΠΎΠΊΡΠΈΠΌΠ΅Ρ‚ΠΈΠ»Ρ‚Ρ–ΠΎΠ»ΡŒΠ½ΠΈΠΌ Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ΠΎΠΌ, Π° Ρ‚Π°ΠΊΠΎΠΆ ΠΏΡ€ΠΎΠ°Π½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½Ρ– Ρ€Π΅Π·ΡƒΠ»ΡŒΡ‚Π°Ρ‚ΠΈ вивчСння Π±Ρ–ΠΎΠ»ΠΎΠ³Ρ–Ρ‡Π½ΠΎΡ— активності Π΄Π°Π½ΠΎΠ³ΠΎ класу сполук. Основними напрямками синтСзу Π°Π·ΠΎΠ»Ρ–Π»Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΡ… кислот Ρ‚Π° Ρ—Ρ… ΠΏΠΎΡ…Ρ–Π΄Π½ΠΈΡ… Π½Π° ΡΡŒΠΎΠ³ΠΎΠ΄Π½Ρ– Ρ” Ρ€Π΅Π°ΠΊΡ†Ρ–Ρ— Π°Π·ΠΎΠ»Ρ–Π², Ρ‰ΠΎ ΠΌΡ–ΡΡ‚ΡΡ‚ΡŒ Ρ‚Ρ–ΠΎΠ»ΡŒΠ½Ρƒ Π³Ρ€ΡƒΠΏΡƒ, Ρ–Π· Π³Π°Π»ΠΎΠ³Π΅Π½ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΠΌΠΈ кислотами Ρ‚Π° Ρ—Ρ… ΠΏΠΎΡ…Ρ–Π΄Π½ΠΈΠΌΠΈ, Π½ΡƒΠΊΠ»Π΅ΠΎΡ„Ρ–Π»ΡŒΠ½Π΅ заміщСння Π³Π°Π»ΠΎΠ³Π΅Π½Ρƒ Π² Π³Π°Π»ΠΎΠ³Π΅Π½ΠΎΠ°Π·ΠΎΠ»Π°Ρ… ΠΏΡ€ΠΈ Π΄Ρ–Ρ— Ρ‚Ρ–ΠΎΠ³Π»Ρ–ΠΊΠΎΠ»Π΅Π²ΠΎΡ— кислоти. ΠžΠΊΡ€Ρ–ΠΌ Ρ†ΡŒΠΎΠ³ΠΎ знайшли застосування приєднання Ρ‚Ρ–ΠΎΠ»Ρ–Π² Π΄ΠΎ ΠΊΡ€Π°Ρ‚Π½ΠΈΡ… зв’язків, Π°ΠΊΡ‚ΠΈΠ²ΠΎΠ²Π°Π½ΠΈΡ… Π΅Π»Π΅ΠΊΡ‚Ρ€ΠΎΠ½ΠΎΠ°ΠΊΡ†Π΅ΠΏΡ‚ΠΎΡ€Π½ΠΈΠΌΠΈ угрупованнями, Π° Ρ‚Π°ΠΊΠΎΠΆ формування азольного Ρ†ΠΈΠΊΠ»Ρƒ Π· Π³Π΅Ρ‚Π΅Ρ€ΠΎΡ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»ΡŒΠ½ΠΈΡ… систСм, які Π²ΠΆΠ΅ ΠΌΡ–ΡΡ‚ΡΡ‚ΡŒ Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΎΡ— кислоти. Для отримання ΠΏΠΎΠ»Ρ–Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»ΡŒΠ½ΠΈΡ… ΠΏΠΎΡ…Ρ–Π΄Π½ΠΈΡ… Π°Π·ΠΎΠ»Ρ–Π»Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΡ… кислот Ρ–Π½ΠΎΠ΄Ρ– Π²ΠΈΠΊΠΎΡ€ΠΈΡΡ‚ΠΎΠ²ΡƒΡ”Ρ‚ΡŒΡΡ Π²Π°Ρ€Ρ–Π°Π½Ρ‚ ΠΌΠΎΠ΄ΠΈΡ„Ρ–ΠΊΠ°Ρ†Ρ–Ρ— Ρ„ΡƒΠ½ΠΊΡ†Ρ–ΠΎΠ½Π°Π»ΡŒΠ½ΠΈΡ… Π³Ρ€ΡƒΠΏ Π°Π·ΠΎΠ»Ρ–Π² Ρ–Π· Π²ΠΆΠ΅ наявним Ρ„Ρ€Π°Π³ΠΌΠ΅Π½Ρ‚ΠΎΠΌ Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΎΡ— кислоти. УзагальнСння Π»Ρ–Ρ‚Π΅Ρ€Π°Ρ‚ΡƒΡ€Π½ΠΈΡ… Π΄Π°Π½ΠΈΡ… Π΄Π°Ρ” всі підстави ствСрдТувати, Ρ‰ΠΎ ΠΏΠΎΡ…Ρ–Π΄Π½ΠΈΠΌ Π°Π·ΠΎΠ»Ρ–Π»Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΡ… кислот властива Ρ€Ρ–Π·Π½ΠΎΠΏΠ»Π°Π½ΠΎΠ²Π° Π±Ρ–ΠΎΠ»ΠΎΠ³Ρ–Ρ‡Π½Π° дія. Π—ΠΎΠΊΡ€Π΅ΠΌΠ°, для Π½ΠΈΡ… Ρ…Π°Ρ€Π°ΠΊΡ‚Π΅Ρ€Π½Π° антиоксидантна, Π³Ρ–ΠΏΠΎΠ³Π»Ρ–ΠΊΠ΅ΠΌΡ–Ρ‡Π½Π°, ΠΏΡ€ΠΎΡ‚ΠΈΡ‚ΡƒΠ±Π΅Ρ€ΠΊΡƒΠ»ΡŒΠΎΠ·Π½Π°, Π°Π½Π°Π»Π³Π΅Ρ‚ΠΈΡ‡Π½Π°, противірусна, Π°Π½Ρ‚ΠΈΠΌΡ–ΠΊΡ€ΠΎΠ±Π½Π° Ρ‚Π° ΠΏΡ€ΠΎΡ‚ΠΈΠ³Ρ€ΠΈΠ±ΠΊΠΎΠ²Π° Π°ΠΊΡ‚ΠΈΠ²Π½Ρ–ΡΡ‚ΡŒ. ΠŸΡ€ΠΎΠ°Π½Π°Π»Ρ–Π·ΠΎΠ²Π°Π½ΠΈΠΉ ΠΌΠ°Ρ‚Π΅Ρ€Ρ–Π°Π» засвідчує ΠΏΠ΅Ρ€ΡΠΏΠ΅ΠΊΡ‚ΠΈΠ²Π½Ρ–ΡΡ‚ΡŒ ΠΏΠΎΡˆΡƒΠΊΡƒ Π½ΠΎΠ²ΠΈΡ… Π±Ρ–ΠΎΠ°ΠΊΡ‚ΠΈΠ²Π½ΠΈΡ… Ρ€Π΅Ρ‡ΠΎΠ²ΠΈΠ½ Π² ряду Π°Π·ΠΎΠ»Ρ–Π»Ρ‚Ρ–ΠΎΠΎΡ†Ρ‚ΠΎΠ²ΠΈΡ… кислот
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