Особливості отримання триазенів антрахінонового ряду

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dc.citation.epage96
dc.citation.issue1
dc.citation.spage92
dc.contributor.affiliationПрикарпатський національний університет імені Василя Стефаника
dc.contributor.affiliationНаціональний університет “Львівська політехніка”
dc.contributor.affiliationVasyl Stefanyk Precarpathian National University
dc.contributor.affiliationLviv Polytechnic National University
dc.contributor.authorТарас, Т. М.
dc.contributor.authorДейчаківський, Ю. І.
dc.contributor.authorШупенюк, В. І.
dc.contributor.authorСабадах, О. П.
dc.contributor.authorБолібрух, Л. Д.
dc.contributor.authorTaras, T. M.
dc.contributor.authorDejchakivsky, Y. I.
dc.contributor.authorShupeniuk, V. I.
dc.contributor.authorSabadakh, O. P.
dc.contributor.authorBolibrukh, L. D.
dc.coverage.placenameLviv
dc.coverage.placenameLviv
dc.date.accessioned2020-02-28T13:09:26Z
dc.date.available2020-02-28T13:09:26Z
dc.date.created2019-02-28
dc.date.issued2019-02-28
dc.description.abstractНадзвичайно важливим показником є висока чистота і стійкість вихідних та проміжних продуктів, які використовують для синтезу триазенів, тому було розглянуто різні способи отримання триазенів антрахінонового ряду, зокрема α- і β-аміно-9,10-антрацендіонів та бромамінової кислоти з амінопохідними. Підібрано оптимальні умови реакції діазотування, N-азосполучення та синтезу із високим виходом передбачуваних триазенів та здійснено їх спектральну ідентифікацію. Мас-спектроскопією високої роздільної здатності досліджено проблему прототропії 2-[2-(морфолін-4-іл) діазеніл] антрацен-9,10-діону з утворенням 2-гідро- ксиантрацен-9,10-діону.
dc.description.abstractA very important indicator is the high purity and stability of the output and intermediate products used for the synthesis of triazenes, therefore various methods for the preparation of triazenes of the anthraquinones series, and in particular α- and β-amino-9,10-anthracenediones and bromaminic acid with amino-derivatives, were considered. The optimal conditions for the reaction of diazotization, N-azo coupling and synthesis with a high yield of triazenes are given and their spectral identification is carried out. The problem of 2-[2-(morpholin-4-yl) diazenyl] anthracene-9,10-dione prototropy with the formation of 2-hydroxyanthracene-9,10-dione was investigated with the high resolution mass spectroscopy (HRMS).
dc.format.extent92-96
dc.format.pages5
dc.identifier.citationОсобливості отримання триазенів антрахінонового ряду / Т. М. Тарас, Ю. І. Дейчаківський, В. І. Шупенюк, О. П. Сабадах, Л. Д. Болібрух // Chemistry, Technology and Application of Substances. — Lviv : Lviv Politechnic Publishing House, 2019. — Том 2. — № 1. — С. 92–96.
dc.identifier.citationenFeatures of synthesis of triazenes of the anthraquinone series / T. M. Taras, Y. I. Dejchakivsky, V. I. Shupeniuk, O. P. Sabadakh, L. D. Bolibrukh // Chemistry, Technology and Application of Substances. — Lviv : Lviv Politechnic Publishing House, 2019. — Vol 2. — No 1. — P. 92–96.
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/46362
dc.language.isouk
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry, Technology and Application of Substances, 1 (2), 2019
dc.relation.references1. Gadjeva V. G. (2002). Two spin labeled triazenes: relationship between biochemical and biological activities Int. J. Pharm. 247, 39–45.
dc.relation.references2. Kimball D. B., HaleyM. M. (2002). Triazenes: A Versatile Tool in Organic Synthesis Angew. Chem. Int. Ed. 41, 3338–3351.
dc.relation.references3. Khramov D. M., Bielawski C. W. (2007). Donor – Acceptor Triazenes: Synthesis, Сharacterization, and study of Their Electronic and Thermal Properties J. Org. Chem. 72 (25), 9407–9417. DOI: 10.1021/jo070789x
dc.relation.references4. Gornostaev L. M., Levdansky V. A. (1980). On the transformations of 1-azido-2- aryloxyanthraquinones and 3-aryloxyanthra [1,9-cd]-6- isoxazolones Russ. J. Org. Chem., Vol. 16, 10, 2209–2215.
dc.relation.references5. Stefane B., Kocevar M., Polanc S. (1997). Nitrosation with Sodium Hexanitrocobaltate J. Org. Chem. 62, 7165–7169.
dc.relation.references6. Baines K. M., Vaughan K., Hooper D. L., Leveck L. F. (1983). Open-chain nitrogen compound. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1- aryl-3-(ethoxycarbonylmethyl) triazenes: a new route to α-diazo-N-arylacetamides Can. J. CHem., 61, 1549–1556.
dc.relation.references7. Bulgakova N. A., Gornostaev L. M., Sakilidi V. T. (2000). Synthesis and structure of some triazenes of the 9,10-anthraquinone series Russ. J. Org. Chem., Vol. 36, 10, 1519–1520.
dc.relation.references8. Bulgakova N. A. (2002). Sintez, struktura i svojstva nekotoryh proyzvodnyh 9,10-antrahinonu, soderzhashhih svjaz' azot-azot [Synthesis, structure and properties of some 9,10-anthraquinone derivatives containing a nitrogen-nitrogen bond]: abstract of the thesis for the degree of Candidate of Chemical Sciences, Krasnoyarsk State Pedagogical University named after V. P. Astafyev, Krasnoyarsk [in Russian].
dc.relation.references9. Wacker L. (1902). Ueber den Austausch der Diazogruppe durch die Amidogruppe Chem. Ber. 35, 2593–2602.
dc.relation.references10. Sabadakh O. P., Taras T. N., Luchkevich E. R., Novikov V. P. (2015). Synthesis of triazene derivatives of 9,10-anthraquinone. Russ. J. Org. Chem., Vol. 51, 2, 277–278. DOI: 10.1134/S1070428015020244
dc.relation.references11. Dejchakivsky Y. I., Luchkevich E. R., Taras T. N., Bolibrukh L. D., Hubytska I. I. (2015). Pro diazotuvannja β-amino-9,10-antrahinonu [About diazotization of β-amino-9,10-anthrahinone] Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 812, 237–238 [in Ukrainian].
dc.relation.references12. Shupeniuk V. I., Dejchakivsky Y. I., Taras T. M., Bolibrukh L. D., Hubytska I. I. (2017). Pro osoblyvosti diazotuvannja aminopohidnyh 9,10- antrahinonu [About features of the diazotization of amino derivatives of 9,10-anthraquinone] Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 868, 186–195 [in Ukrainian].
dc.relation.references13. Shupeniuk V. I., Taras T. M., Bolibrukh L. D., Zhurakhivska L. R., Hubytska I. I. (2018). Interaction between structure and activity of synthesize triazenes at 4-substituted 9,10- anthraquinone. Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 868, 136–145 [in Ukrainian].
dc.relation.references14. Bulgakova N. A., Gornostaev L. M. (2001). Cyclization of 1-Aryl-3-[4-aryl (cyclohexyl) amino-9,10-dioxo-1-anthryl] triazenes to 3-Aryl-5-aryl (cyclohexyl)-aminoanthra [1,2 d][1,2,3] triazole-6,11-diones. Russian Journal of Organic Chemistry, vol. 37, no. 9, 1351–1352.
dc.relation.references15. Amoroso J. W. (2014). Reactive Probes for Manipulating Polyketide Synthases, and Photoreactive Probes for Strained Alkyne Click Chemistry (Doctoral Dissertations). University of Massachusetts – Amherst.
dc.relation.referencesen1. Gadjeva V. G. (2002). Two spin labeled triazenes: relationship between biochemical and biological activities Int. J. Pharm. 247, 39–45.
dc.relation.referencesen2. Kimball D. B., HaleyM. M. (2002). Triazenes: A Versatile Tool in Organic Synthesis Angew. Chem. Int. Ed. 41, 3338–3351.
dc.relation.referencesen3. Khramov D. M., Bielawski C. W. (2007). Donor – Acceptor Triazenes: Synthesis, Sharacterization, and study of Their Electronic and Thermal Properties J. Org. Chem. 72 (25), 9407–9417. DOI: 10.1021/jo070789x
dc.relation.referencesen4. Gornostaev L. M., Levdansky V. A. (1980). On the transformations of 1-azido-2- aryloxyanthraquinones and 3-aryloxyanthra [1,9-cd]-6- isoxazolones Russ. J. Org. Chem., Vol. 16, 10, 2209–2215.
dc.relation.referencesen5. Stefane B., Kocevar M., Polanc S. (1997). Nitrosation with Sodium Hexanitrocobaltate J. Org. Chem. 62, 7165–7169.
dc.relation.referencesen6. Baines K. M., Vaughan K., Hooper D. L., Leveck L. F. (1983). Open-chain nitrogen compound. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1- aryl-3-(ethoxycarbonylmethyl) triazenes: a new route to α-diazo-N-arylacetamides Can. J. CHem., 61, 1549–1556.
dc.relation.referencesen7. Bulgakova N. A., Gornostaev L. M., Sakilidi V. T. (2000). Synthesis and structure of some triazenes of the 9,10-anthraquinone series Russ. J. Org. Chem., Vol. 36, 10, 1519–1520.
dc.relation.referencesen8. Bulgakova N. A. (2002). Sintez, struktura i svojstva nekotoryh proyzvodnyh 9,10-antrahinonu, soderzhashhih svjaz' azot-azot [Synthesis, structure and properties of some 9,10-anthraquinone derivatives containing a nitrogen-nitrogen bond]: abstract of the thesis for the degree of Candidate of Chemical Sciences, Krasnoyarsk State Pedagogical University named after V. P. Astafyev, Krasnoyarsk [in Russian].
dc.relation.referencesen9. Wacker L. (1902). Ueber den Austausch der Diazogruppe durch die Amidogruppe Chem. Ber. 35, 2593–2602.
dc.relation.referencesen10. Sabadakh O. P., Taras T. N., Luchkevich E. R., Novikov V. P. (2015). Synthesis of triazene derivatives of 9,10-anthraquinone. Russ. J. Org. Chem., Vol. 51, 2, 277–278. DOI: 10.1134/S1070428015020244
dc.relation.referencesen11. Dejchakivsky Y. I., Luchkevich E. R., Taras T. N., Bolibrukh L. D., Hubytska I. I. (2015). Pro diazotuvannja b-amino-9,10-antrahinonu [About diazotization of b-amino-9,10-anthrahinone] Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 812, 237–238 [in Ukrainian].
dc.relation.referencesen12. Shupeniuk V. I., Dejchakivsky Y. I., Taras T. M., Bolibrukh L. D., Hubytska I. I. (2017). Pro osoblyvosti diazotuvannja aminopohidnyh 9,10- antrahinonu [About features of the diazotization of amino derivatives of 9,10-anthraquinone] Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 868, 186–195 [in Ukrainian].
dc.relation.referencesen13. Shupeniuk V. I., Taras T. M., Bolibrukh L. D., Zhurakhivska L. R., Hubytska I. I. (2018). Interaction between structure and activity of synthesize triazenes at 4-substituted 9,10- anthraquinone. Journal of Lviv Polytechnic National University Series of Chemistry, Materials Technology and their Application, 868, 136–145 [in Ukrainian].
dc.relation.referencesen14. Bulgakova N. A., Gornostaev L. M. (2001). Cyclization of 1-Aryl-3-[4-aryl (cyclohexyl) amino-9,10-dioxo-1-anthryl] triazenes to 3-Aryl-5-aryl (cyclohexyl)-aminoanthra [1,2 d][1,2,3] triazole-6,11-diones. Russian Journal of Organic Chemistry, vol. 37, no. 9, 1351–1352.
dc.relation.referencesen15. Amoroso J. W. (2014). Reactive Probes for Manipulating Polyketide Synthases, and Photoreactive Probes for Strained Alkyne Click Chemistry (Doctoral Dissertations). University of Massachusetts – Amherst.
dc.subject2-[2-(морфолін-4-іл) діазеніл] антрацен-9
dc.subject10-діон
dc.subjectбромамінова кислота
dc.subjectдіазотування
dc.subjectN-азосполучення
dc.subjectα-аміноантрацен-9
dc.subject10-діон
dc.subjectβ-аміноантрацен-9
dc.subject10-діон
dc.subjectхромато-мас-спектр
dc.subject2-[2-(morpholin-4-yl) diazenyl] anthracene-9
dc.subject10-dione
dc.subjectbromaminic acid
dc.subjectdiazotization
dc.subjectN-azocoupling
dc.subjectα-aminoanthracene-9
dc.subject10-dione
dc.subjectβ-aminoanthracene-9
dc.subject10-dione
dc.subjectchromaticmass spectrum
dc.titleОсобливості отримання триазенів антрахінонового ряду
dc.title.alternativeFeatures of synthesis of triazenes of the anthraquinone series
dc.typeArticle

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Chemistry, Technology and Application of Substances. – 2019. – Vol. 2, No. 1