Laboratory of Sulfur Chemistry (2013)

 

The Head of the Laboratory

Doctor of Chemical Sciences, Associate Professor Rozentsveig Igor Borisovich

Phone: +7(3952)511434, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

Number of Employees: 13 researchers, 4 engineers, 1 postgraduate student, including 4 Dr.Sc. (Habilitated), 9 Ph.D. (Chemistry).

Staff:

1. Mirskova Anna Nikolaevna, Professor, D.Sc., Principal researcher,

Phone: +7(3952)424711, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

2. Levkovskaya Galina Grigor’evna, Professor, Dr.Sc. Leading researcher,

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3. Papernaya Lyubov Konstantinovna, D.Sc., Senior researcher,

Phone: +7(3952)424911, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

4. Levanova Ekaterina Petrovna, PhD, Senior researcher,

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5. Grabelnykh Valentina Alexandrovna, Ph.D., Scientific associate,

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6. Aizina Yuliya Alexandrovna, Ph.D., Scientific associate,

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7. Popov Alexander Vitalievich, Ph.D., Scientific associate,

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8. Kondrashov Eugeniy Vladimirovich, Ph.D., Scientific associate,

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9. Rudyakova Elena Vladimirovna, Ph.D., Scientific associate,

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10. Kobelevskaya Valentina Alexandrovna, Ph.D., Scientific associate,

Phone: +7(3952)424911

11. Chernysheva Gulnur Nabiullovna, Ph.D., Scientific associate,

Phone: +7(3952)424911, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

12. Serykh Valery Yurievich, Ph.D., Junior Researcher,

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13. Shatrova Alexandra Alexandrovna, Ph.D., Engineer,

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14. Kupriyanova Nina Sergeevna, Leading engineer,

Phone: +7(3952)424911, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

15. Fedotova Alyona Igorevna, Engineer,

Phone: +7(3952)424911

16. Pinchuk Snezana Olegovna, Engineer,

Phone: +7(3952)424911

17. Vakhrina Valentina Sergeevna, Postgraduate student,

Phone: +7(3952)424911, e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

18. Korchevin Nikolai Alekseevich, Professor, D.Sc., Scientific consultant,

phone +7 (3952) 424911 , e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

Areas of Research

— development of new general methods;

— study of mechanism and regularities of molecule formations and reactivity of new sulfides, sulfonamides, azoles synthesized.

Principal results

1. A new research approach to chemistry of nitrogen-containing haloorganic compounds on the basis of industrial reagents has been developed. Selective synthesis of functionalized sulfonamide derivatives has been elaborated, including polyhaloethylsulfonamides, amidines, amino acids, aminocarbonyl compounds, as well as benzofuran, aziridine, thiazole, imidazole heterocyclic derivatives. Among the compounds synthesized some biologically active substances exhibiting properties of microbial growth promoters, herbicides, insectoacaricides have been found.

Researchers: Levkovskaya G.G., Mirskova A.N., Rozentsveig I.B., Aizina Yu. A., Kondrashov E.V., Chernysheva G.N., Serykh V.Yu., Popov A.V.

2. An unusual reaction of chloroacylchlorides with 1,2-dichloroethylene has been elaborated. The process is accompanied by chlorotropic and prototropic rearrangements and leads to (β-chlorovinyl)(α,α-dichloroalkyl)ketones.

Researchers: Levkovskaya G.G., Popov A.V., Rudyakova E.V., Kobelevskaya V.A.

3. An efficient methodology for the synthesis of formylpyrazoles, chloroalkyl- and alkenylsubstituted derivatives of pyrazole series has been developed and their functionalizations with S-, Se-, N-, P-nucleophiles, polynucleophiles and radicals have been studied. The approaches to obtain promising reagents, ligands, insectoacaricides, containing pyrazole cycles in their structures have been reached.

Researchers: Levkovskaya G.G., Papernaya L.K., Popov A.V., Rudyakova E.V., Kobelevskaya V.A., Shatrova A.A.

4. General efficient methods to obtain a wide range of organic sulfur derivatives and selenium or tellurium analogues started from the elemental chalcogens and haloorganic compounds, including those that are byproducts and waste products of chloroorganic industrial manufacturing, have been developed. New fundamental information about the reactivity of haloorganic compounds, chalcogen containing nucleophiles and their complementarity as reagents has been gained.

Researchers: Korchevin N.A., Rozentsveig I.B., Levanova E.P., Grabelnykh V.A., Vakhrina V.S.

5. A general methodology for targeted synthesis of biologically active derivatives of organylheteroalkanecarboxylic acids has been studied systematically and their biological activity have been tested. The compounds exhibiting erythropoiesis immunomodulating properties and antiinflammatory, anticancer, antioxidant, antiaggregatory activities in combination together with harmlessness for warm-blooded organisms have been discovered. Promoters for the growth of microorganisms and plants have been developed. The compounds synthesized are the promising agents for drugs, for example, drugs against allergy or for medical treatments of autoimmune and immunodeficiency affections, drugs and cures for anemic, cancer and vascular diseases, as well as they could be applied as adjuvants for transplantation of organs and bone-marrows, for the prevention of stress developments, and for increasing the resistance of live organisms to harmful affects of microwave radiation.

Researchers: Mirskova A.N., Levkovskaya G.G.

Innovative developments

— Indacetamine is a promising immunomodulator of erythropoiesis with selective T-limphotropic action, efficient in small doses (2-5 mg/kg). It is a new generation drug for the treatment of autoimmune diseases (rheumatism, systemic lupus erythematosus, vasculitis, immunocomplex glomerulonephritis, rheumatoid arthritis, acute virus hepatitis and etc.), lingering and chronic inflammations, tumors and anemias, as well as for the prophylaxis of acute respiratory and viral infections. Unlike cyclosporine A, Indacetamine produces no nephritotoxic and hepatotoxic action. It decreases and relieves inflammation of liver tissue in hepatitis, prevents degeneration of hepatitis to cirrhosis, and stops the inflammation of kidney tissue in immunocomplex glomerulonephritis, also arrests the inflammation of connective tissue. It has an effective protective action in traumatic cardiogenic shock and toxic stress.

Contact person: Mirskova A.N.

— “ROST” Preparation (“Growth”) is intended for raising the level of crop yield (cereals, vegetables, seeds, forage grasses and herbs).

Contact person: Mirskova A.N.

— Chlorocrezacyn is a new original medicament, promising to protect human organisms from shock and stress states, has anti-toxic and anti-ulcerous effects, increases the resistance of organism to harmful affects of microwave radiation, and stimulates erythropoiesis, as well as manifests immunomodulating, antitumor and antimetastatic activities.

Contact person: Mirskova A.N.

— The method for short-time (cut-time) of staphylococcus diagnostics. The method reduces the time (from 48 to 6-9 h) of staphylococcus analysis that optimizes the time of antibiotic treatment for patients, especially, for those of social impact, caused by nosocomial purulent-inflammatory infections in surgical, obstetric and pediatric hospitals.

Contact person: Mirskova A.N.

— Sulfacetamine is a non-toxic, ecologically benign growth factor of baker’s yeast and pale malt, antioxidizer, it allows to increase the yield and quality of the products, increases the productivity and cheapens production, improves the quality of bread. It can be used in the production of yeasts, malt, citric acid, feed protein and biomasses of various microorganisms by using of paraffin, natural gas, alcohols, fatty acids and hydrocarbons as starting materials. The Ministry of Health of Russia approves the application of Sulfacetamine in food industry.

Contact person: Levkovskaya G.G.

— A broth on the basis of “Fenthiol” for the selective isolation of Ps. Aeruginosa. It is designed for the selective isolation of pigmental and amelanotic strains of Ps. Aeruginosa of a pure culture in the presence of microbial associations including the Proteus group. The broth is recommended for use in bacteriological laboratories for the study of purulent discharge of surgical patients. It is tested by the Institute of Epidemiology and Microbiology SB RAMS and recommended for application.

Contact person: Papernaya L.K.

— Flotation agents to intensify the process of enrichment of polymetallic ores.

Contact person: Levkovskaya G.G.

— Sulfur containing sorbents from waste products of epichlorohydrin manufacture that is substandard petroleum coke (particle diameter of less than 0.15 mm), the latter is also the waste product of metallurgical industries.

Contact person: Rozentsveig I.B.

— A method for obtaining of nanoparticles of AIIBVI type, stabilized by organylchalkogenide fragments.

Contact person: Rozentsveig I.B.

 

— A method for obtaining of volatile organic compounds of selenium and tellurium, which are used in manufacturing of ultrapure elements and for growing epitaxial layers of semiconductor compounds like AIIBVI type.

Contact person: Rozentsveig I.B.

— A burnished additive DK-8, to accelerate the burnish of diesel engines after their repair.

Contact person: Rozentsveig I.B.

— Catalyst of rosin clarification (disproportionation).

Contact person: Rozentsveig I.B.

— A general methodology for the preparation of thiophene and selenophene.

Contact person: Rozentsveig I.B.

Awards

· The diploma “The Heritage of Siberia” in the nomination of <Science and Education> for the contribution into Siberian Science was awarded to Rozentsveig I.B. (2007).

· Honorary Medals “350 Years of Irkutsk” — Mirskova A.N., Levkovskaya G.G., Levanova E.P., Papernaya L.K., Kuprianova N.S. (2012).

· Honorary Medals of the Siberian Branch of the Russian Academy of Sciences “Silver Sigma” — Mirskova A.N., Levkovskaya G.G., Levanova E.P., Papernaya L.K., Kuprianova N.S.. (2007).

· Diploma of the Governor of Irkutsk Region - Rozentsveig I.B (2012).

Promotions for the last four years

Serykh V.Yu. “Addition and heterocyclization reactions of polychloroethylidene- and polychloroethylsulfonamides” Ph.D. Thesis, 2012. Scientific leader: Rozentsveig I.B.

Samultsev D.O. “3-Alkenylpyrazoles. Directed synthesis and study of the reactivity” Ph.D. Thesis 2012. Scientific leader: Levkovskaya G.G.

Shatrova A.A. “Thio- and selenoacetalization of pyrazolecarbaldehydes in the presence of alkylchlorosilanes” Ph.D. Thesis 2013. Scientific leader: Papernaya L.K.

Our partners of joint research works and agreements

— Irkutsk Antiplague Research Institute of Siberia and Far East.

— Irkutsk State University.

— Irkutsk Scientific Research Institute of precious and rare metals and diamonds.

— Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus.

— Angarsk branch of Research Institute of Human Labor and Ecology SB RAMS.

— National Research Irkutsk State Technical University.

Grants and contracts

— Program: “Basic sciences for medicine”.

Project: “Devising research methodology for the targeted synthesis of 2-hydroxyethylammonium salts of indole-3-ylsulfanyl(sulfonyl)- and pyrrole-2-ylsulfanylalkanecarboxylic acids, the new biologically active compounds to develop a new generation drugs with immuno-, hemopoezmodulating and antitumor activities.” (Principal — Mirskova A.N.)

— Program: “Basic sciences for medicine”

Project: “Elaboration of original drug INDACETAMIN- immunosuppressant with selective action mechanism.” (Principal — Mirskova A.N.)

Government contractual works on research for the RF Ministry of Defense.

— RFBR Grant No.10-03-00256-a “Mechanism of polyheterocyclic structures formations at acetalization of formylsubstituted heteroarenes in trimethylchlorosilane medium”. (Principal — Papernaya L.K.)

— RFBR Grant No. 11-03-00461-a “Research and development of new reactions of 2-haloacylhalogenides with 1,2-polyhaloethenes and concept of halogenotropic rearrangements. Target synthesis of polyhaloenones and 3-alkenylpyrazoles based on them”. (Principal Levkovskaya G.G.)

— RFBR Grant No. 12-03-31762 mol_a “Functionalized annulated azole systems: a new approach to the synthesis and study of their properties”. (Principal — Chernysheva G.N.)

— Grant for joint fundamental researches of Belarus NAS and the SB RAS (project № 21) entitled “New highly reactive functionalized halogenenones and imines based on industrial chloro-organic and sulfur-organic raw materials for target synthesis of useful products”. (Principal — Levkovskaya G.G.)

Publications in 2010-2013

2010-2011

· Rozentsveig I.B., Popov A.V., Rozentsveig G.N., Serykh V.Yu., Chernyshev K.A., Krivdin L.B., Levkovskaya G.G. A novel regiospecific cascade synthesis of sulfonamide derivatives from N-(2-polychloroethyl)sulfonamides via chloroaziridine intermediates in the presence of mercaptoethanol // Mol. Divers. — 2010. — V. 14. — № 3. — P. 533-525. DOI: 10.1007/s11030-010-9231-z

· Nenajdenko V.G., Muzalevskiy V.M., Shastin A.V., Balenkova E.S., Kondrashov E.V., Ushakov I.A., Rulev A.Yu. Fragmentation of Trifluoromethylated Alkenes and Acetylenes by Binucleophiles. Synthesis of Imidazolines or Imidazolidines (Oxazolidines) Controlled by Substituent // J. Org. Chem. — 2010. — V. 75. — P. 5679-5688.

· Levkovskaya G.G., Kobelevskaya V.A., Rudyakova E.V., Ha K.Q., Samultsev D.O., Rozentsveig I.B. 3-Alkenyl-5-chloropyrazoles: expedient synthesis via heterocyclization of 1,1-dichloro-4-halo-1-alken-3-ones with hydrazines // Tetrahedron. — 2011. — V.67, Issue 10. — P. 1844-1851.

· Rozentsveig I.B., Rozentsveig G.N., Serykh V.Yu., Chernyshev K.A., Levkovskaya G.G. A New Synthesis of 3-(Sulfonamido)benzofurans through an Acid-Promoted Cascade Reaction of N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides with para-Substituted Phenols // Eur. J. Org. Chem. — 2011. — Issue 23. — P. 4415–4421.

· Adamovich S.N., Mirskova A.N., Mirskov R.G., Schilde U. Synthesis and crystal structure of 1,4,10,13-tetraoxa-7,16-diazoniumcyclooctadecane bis(4-chloro-2-methyl-phenoxyacetate) // Chemistry Central Journal. — 2011. V. 5:23.

· Rozentsveig I.B., Rozentsveig G.N., Levkovskaya G.G., Amosova S.V., Potapov V.A., Chernyshev K.A., Tretyakov E.V., Romanenko G.V. Unexpected reaction of N,N-dichloroarenesulfonamides with divinyl sulfide: formation of N-[2-chloro- and N-[2,2-dichloro-1-(arylsulfonylamino)ethyl]arenesulfonamides // Arkivoc — 2011. — (x). — P. 182-192.

· Aizina Ju.A., Rozentsveig I.B., Levkovskaya G.G. A novel synthesis of chloroacetamide derivatives via C-amidoalkylation of aromatics by 2-chloro-N-(2,2,2-trichloro-1-hydroxyethyl)acetamide // Arkivoc. — 2011. — (viii). — P. 192-199.

2012

· Chipanina N.N., Aksamentova T.N., Adamovich S.N., Albanov A.I., Mirskova A.N., Mirskov R.G., Voronkov M.G. The proton transfer and hydrogen bonding complexes of (2-hydroxyethyl)amines with acids. A theoretical study // Computational and Theoretical Chemistry — 2012. — V. 985. — P. 36–45.

· Papernaya L.K., Shatrova A.A., Albanov A.I., Klyba L.V., Levkovskaya G.G. Nitroaromatic bis(2-hydroxyethyl)dithioacetals and oxathioacetals using 2-mercaptoethanol in the presence of chlorosilanes // Arkivoc — 2012. — (vi). — P. 173-184.

· Levanova E.P., Grabelnykh V.A., Elaev A.V., Albanov A.I., Klyba L.V., Russavskaya N.V., Tarasova O.A., Rozentsveig I.B., Korchevin N.A. Unexpected reaction of 2-chloro-1-propen-3-yl isothiuronium chloride with potassium ditelluride: the first example of vicinal elimination of chlorine and sulfur-bearing moieties // J. Sulf. Chem. — 2012. — V. 33, № 5. — P. 505-511.

· Adamovich S.N., Mirskova A.N., Mirskov R.G., Lopyrev V.A. Synthesis of novel benzimidazolium salts of biologically active chalcogenylacetic acids // Mendeleev Comm. — 2012. — V. 22. № 6. — P. 330-331.

2013

· Rozentsveig I.B., Serykh V.Y., Chernysheva G.N., Chernyshev K.A., Kondrashov E.V., Tretyakov E.V., Romanenko G.V. One-Pot Synthesis of N-(Imidazo[1,2-a]pyridin-3-yl)- and N-(Imidazo[2,1-b][1,3]thiazol-5-yl)sulfonamides // Eur. J. Org. Chem. — 2013. — P. 368–375. 
DOI: 10.1002/ejoc.201201006

· Rulev A.Yu., Muzalevskiy V.M., Kondrashov E.V., Ushakov I.A., Romanov A.R., Khrustalev V.N., Nenajdenko V.G. Reaction of -Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement // Org. Lett. — 2013. — V. 15, № 11. — P. 2726-2729. DOI: 10.1021/ol401041f

· Mirskova A.N., Adamovich S.N., Mirskov R.G., Schilde U. Reaction of pharmacological active tris-(2-hydroxyethyl)ammonium 4-chlorophenylsulfanylacetate with ZnCl2 or NiCl2: first conversion of a protic ionic liquid into metallated ionic liquid // Chem. Central J. — 2013. — 7:34. DOI: 10.1186/1752-153X-7-34

· Papernaya L.K., Shatrova A.A., Levanova E.P., Albanov A.I., Rudyakova E.V., Levkovskaya G.G. Synthesis of linear chain 1,1’-bis[(1,3-diselenan-2-yl)pyrazoles] from bisformylpyrazoles and propane-1,3-diselenol // Mendeleev Commun. — 2013. — V. 23, N. 6. — P. 342-343. DOI: 10.1016/j.mencom.2013.11.013

· Papernaya L.K., Shatrova A.A., Levanova E.P., Albanov A.I., Klyba L.V., Rudyakova E.V., Levkovskaya G.G. Selenoacetalyzation of 4-Formylpyrazoles in the Presence of Trimethylchlorosilane // Heteroatom chemistry. — 2013. — 24, Issue 6. — P. 466-475. DOI: 10.1002/hc.21110

 

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