Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)

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The Synthesis of New Organoselenium Heterocyclic Compounds: 2,4-Diaryl-5,6,7,8-Tetrahydroselenochromilium’s Salts

Direnko D. Yu., Central Research Institute of Engineering Troops named after D.M. Karbyshev of the Ministry of Defense of Russia
Drevko Yaroslav B., Saratov State Agrarian University named after V.I. Vavilov.
Drevko B. I., Saratov State Agrarian University named after V.I. Vavilov.

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.


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