The Synthesis of New Organoselenium Heterocyclic Compounds: 2,4-Diaryl-5,6,7,8-Tetrahydroselenochromilium’s Salts
The synthesis of novel organoselenium heterocyclic compounds is of great theoretical and practical interest because of high biological activity. The known methods of synthesis of hexatomic selenium containing heterocyclic compounds allow us to obtain only monoaryl-substituted tetrahydroselenochromilium salts. In this study, the reactions of 2-(3-oxo-1-aryl-3-phenylpropyl) cyclohexanones were carried out with hydrogen selenide in situ under conditions of acid catalysis in diethyl ether. Also the new 2,4-diaryl-5,6,7,8- tetrahydroselenochromilium salts were synthesized with the corresponding yields of 28–50%. The synthesized 2,4-diaryl5,6,7,8-tetrahydroselenochromilium chlorozincate practically didn’t dissolve in all known and available solvents. This fact didn’t allow us to carry out the GC-MS and the 1H NMR directly. Therefore, the salts were identified by converting them into the corresponding perchlorates using the known method. While analyzing 1H NMR spectra of 2,4-diaryl-5,6,7,8-tetrahydroselenochromilium pегсhloratеs it was revealed that they were corresponded to the data of mass spectrometry. The data of 1H NMR showed that the spectra contain the aromatic protons in the form of multiplets with chemical shifts in the fields of 6.61–6.68 ppm and 7.11– 7.33 ppm. Also signals of multiplets of methylene groups of alicyclic fragment of the molecule with chemical shifts in the fields of 0.81–0.92 ppm, 1.18–1.35 and 1.45–1.82 ppm were observed. Keywords: 2,4-Diaryl-5,6,7,8-tetrahydroselenochromilium’s salts; Synthesis; 2-(3-Oxo-1,3-diarylpropyl)cyclohexanones.
1. Ha Herena Y., Alfulaij Naghum, Berry Marla J., Seale Lucia A. From Selenium Absorption to Selenoprotein Degradation. Biological Trace Element Research. Springer Science+Business Media, LLC, part of Springer Nature 2019. DOI: https://doi.org/10.1007/s12011-019-01771-x
2. Ying Huimin, Zhang Yan. Systems Biology of Selenium and Complex Disease. Biological Trace Element Research. Springer Science+Business Media, LLC, part of Springer Nature 2019. DOI: https://doi.org/10.1007/s12011-019-01781-9
3. De Rosa Viviana, Pinar Erkekog Lu, Forestier Anne, Favie Alain r, Hincal Filiz, Diamond Alan M., Douki Thierry, Rachidi Walid. Low doses of selenium specifi - cally stimulate the repair of oxidative DNA damage in LNCaP prostate cancer cells. Free Radical Research, 2012, February, vol. 46, no. 2, pp. 105–115. DOI: https://doi.org/10.3109/10715762.2011.647009
4. Sneddon Alan A. Selenium and vascular health. Pure Appl. Chem., 2012, vol. 84, no. 2, pp. 239–248. DOI: https://doi.org/10.1351/PAC-CON-11-09-01
5. Gigienicheskie kriterii sostoyaniya okruzhayushchei sredy. Selen [Hygienic Criteria of the Environment State. 58. Selenium]. Geneva, The World Health Organization, 1989. 270 p.
6. Pankratov A. N., Tsivileva O. M., Tsymbal O. A., Drevko Ya. B., Tumskii R. S., Marakaeva A. V. Exploration of Possibilities for Organic Selenides and Dihydroselenochromilium Salt Interaction with Diphenylpicrylhydrazyl. Izv. Saratov Univ. (N. S.), Ser. Chemistry. Biology. Ecology, 2019, vol. 19, iss. 1, pp. 39–49 (in Russian). DOI: https://doi.org/10.18500/1816-9775-2019-19-1-39-49
7. Fedotova O. V., Lin’kova E. I., Nazarov V. A., Leontiev Yu. G., Gusakova N. N. Novel Selenium-Organic Compounds as Biologically Active Substances for Enhancing the Stress Stability of Grain and Flower Cultures to Heavy Metals. Izv. Saratov Univ. (N. S.), Ser. Chemistry. Biology. Ecology, 2012. vol. 12, iss. 1. pp. 6–10 (in Russian).
8. Kuthan J., Scebek P., Bouhm S. Developments in the chemistry of thiopyrans, selenopyrans, and teluropyrans. Advances in Heterocyclic Chemistry, 1994, vol. 59, pp. 179–244.
9. Doddi G., Gianfranco E. Thiopyrylium, Selenopyrylium, and Telluropyrylium Salts. Advances in Heterocyclic Chemistry, 1994, vol. 60, pp. 65–195.
10. Detty M. R., Murray B. J., Seidberg M. D. Preparaition of 2,6-difenyl-4H-chalcogenopyran-4-ones. J. Org. Chem., 1982, vol. 47, pp. 1968–1969.
11. Drevko B. I., Fomenko L. A., Smuhskin M. I., Zhukov O. I., Kharchenko V. G. Synthesis of 5,6-polymethyleneselenopyryllium salts. Chemistry of Heterocyclic Compounds, 1994, vol. 30, no. 6, pp. 503–504.
12. Sommen Geoffroy L., Thomae David. Utility of Hydrogen Selenide and Its Related Salts for the Synthesis of Selenium-Containing Heterocycles. Current Organic Synthesis, 2010, vol. 7, no. 1, pp. 44–61.
13. Elsherbini M., Hamama W. S., Zoorob H. H. Recent Advances in the Chemistry of Selenium-Containing Heterocycles: Six-Membered Ring Systems. Coordination Chemistry Reviews, 2017, vol. 330, pp. 110–126. DOI: https://doi.org/10.1016/j.ccr.2016.09.016
14. Pat. 2367658 RF, MPK C07D 345/00. Sposob poluchenija soley selenopyriliya [The method of obtaining salts zelenopillia]. Drevko B. I., Timofeev D. V., Direnko D. Yu., Komissarov A. V., Almaeva A. F. Zayavleno 30.07.2007 № 2007129214/04; Published 20.09.2009, bull. № 26.
15. Putta V. P. R. K., Gujjarappa R., Tyagi U., Malakar C. C., Pujar P. P. A metala nd base-free domino protocol for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines and related scaffolds. Organic & Biomolecular Chemistry, 2019, vol. 17, no. 9, pp. 2516–2528. DOI: https://doi.org/10.1039/c8ob03058h
16. Rucilova V., Soural M. Recent advances in the applications of triethylsilane in organic synthesis. Synthesis, 2018, vol. 50, no. 19, pp. 3809–3824. DOI: https://doi.org/10.1055/s0037-1610107
17. Drevko B. I., Suchkova E. V., Baranchikova G. A., Mandych V. G. New rearrangement of 2,4,6-triarylthio(seleno) pyrylium salts. Russian Chemical Bulletin, Internetional Edition, 2006, vol. 55, no. 10, pp. 1800–1801 (in Russian).