Postovsky Institute of Organic Synthesis - Eurasian Chemical Institutions

Postovsky Institute of Organic Synthesis, Ekaterinburg, Russia

http://www.ios.uran.ru

Research Goals of the Institute of Organic Synthesis of RAS (Ural Division)

One of the main purposes of the Institute is a realization of basic research in the field of organic synthesis which includes synthesis and studying properties of organic compounds, polymers and materials. Besides that, IOS provides professional post-graduate training courses for five specialities:

02.00.02 – Analytical Chemistry,

02.00.03 – Organic Chemistry,

02.00.06 – High-molecular Compounds,

05.17.04 – Technology for Organic Substances,

05.17.07 – Chemical Technology of Fuels and Polymers;

as well as a post-doc training course on Organic Chemistry (02.00.03).

Description of the main scientific investigations of IOS

The main trends of research are given below :

(1) Development, screening and search for medicines; conducting the toxicological investigations:

development of new methodologies for the synthesis of biologically actives in the series of heterocycles, fluorine-organic compounds and amino acids.

(2) Environmental studies:

Design of new compounds and materials based on using of polychlorinated biphenyls;

Design of resource-saving methods of coals processing.

(3) Organic and inorganic synthesis:

Theory of chemical bond, mechanisms of organic reactions, reactivity, structure and properties of organic compounds, stereo chemistry;

Design of new materials based on metal-complex compounds and metal-containing polymers;

Study of fossil coals and development of new theoretical concepts on their structure.

Partners

Experimental plant of RAS in Bolgograd

The State Missile Center and Design Bureau named after academician V.P. Makeev

The Blochin All-Russia Cancer Research Center of the Russian Academy of Medical Sciences

Pharmaceutical Firm “Yunona”

Technologies available in the Institute. Experience and knowledge of the scientists working at the Institute in the field of research and development.

Synthesis of organic compounds, including biologically actives, polymers, etc.

Detailed study of structures of a wide number of organic and bio-organic, including natural compounds; identification and certification of composition and structure of the target and intermediate products of fine organic synthesis; highly effective and high-accuracy quality control of the new developed medicines, along with their metabolic products; the ecological monitoring of technogenic environmental pollution; investigations of mechanisms of organic reactions based on the study of kinetics and structure of intermediates.

Determination of the kinetic (relaxation time) and activation (enthalpy, entropy, energy) parameters of polarization processes proceeding in solid polymers at temperatures ranging from 20 to 250 ° С.

Catalyst testing in the automatic regime at the scaled-up processes (productivity up to 1 kg/h) aimed at the optimization of vapor-phase catalytic processes.

Studying mechanisms and pharmacokinetics for compounds possessing anti-radiation activity.

Utilization of wastes in manufacture of organic compounds, including highly toxic wastes, such as, for example, polychlorinated biphenyls.

Equipment

Institute of Organic Synthesis has unique up-to-date equipment for conducting the synthesis of organic compounds:

High-pressure Instrument (Barostat) for conducting chemical reactions at pressures up to 15,000 atmospheres;
Catalytic pilot installation К L-2;
14 C-Labeled amino acids, counting equipment for beta and gamma sources, equipment for conducting the synthesis of compounds labeled by radionuclides.

unique equipment for conducting the investigations of organic compounds:

NMR Spectrometer DRX-400, «Bruker BioSpin» (Germany);
Chromato-mass-spectrometer QP-2010, «Shimadzu» (Japan);
FTIR Spectrometer Spectrum One B, «Perkin Elmer» (USA);
2400 Series II CHN Analyzer, «Perkin Elmer» (USA);
HPLC Agilent 1100, “Agilent Technologies” (USA);
Unique Dielectric Installation Most Т R-9701 for investigations of temperature-frequency dependence of dielectric properties (Frequency range 0.5 ÷ 200 KHz, measurements of the dielectric power factor, tg δ, from 1 to 1000 ´ 10 -4, the measurement of the electrical capacitance измерения емкости , from 1 ´ 10 -11 to 1 ´ 10 -6.

General organizational structure of the Institute.

In the Institute there are three main subdivisions:

scientific research one, including six Laboratories and three Groups;
administrative;
financial and economic subdivision.

The Institute is headed by Prof. Valery N. Charushin, Full Member of the Russian Academy of Sciences. The scientific supervisor of the Institute is Full Member of RAS, Prof. Oleg N. Chupakhin. Management of the Institute activity is also achieved by the officials and Academic Board of the Institute.

Subdivisions of the Institute

Nine scientific subdivisions, including six Laboratories:

Laboratory of Theoretical Problems of Organic Chemistry, Head of the Lab Prof. Valery N. Charushin, Full Member of RAS;
Laboratory of Heterocyclic Compounds, Head of the Lab
Prof. Oleg N. Chupakhin, Full Member of RAS;
Laboratory of Fluoro-organic Compounds, Head of the Lab
Prof. Victor I. Saloutin;
Laboratory of Amino Acids Chemistry, Head of the Lab
Prof. Victor P. Krasnov;
Laboratory of Organoelement Polymers, Head of the Lab
Dr. Aleksey L. Suvorov;
Laboratory of Coal Chemistry, Head of the Lab
Prof. Evgeny I. Andreykov;

and three Groups:

Group of Catalytic Processes
Head of the Group: Prof. Lev A. Petrov;
Group of Element Analysis
Head of the Group: Dr. Lyudmila N. Bazhenova;
Group of NMR and IR Spectroscopy
Head of the Group: Dr. Mikhail I. Kodess.

The Center of joint usage of the unique equipment of the Ural Division of RAS “Spectroscopy and Analysis of Organic Compounds” is acting on the base of the Institute.

Scientific Staff of the Institute.

Personnel and age structure of the Institute in 2004 (in brackets the mean age is given). The whole staff of the Institute is about 123 persons (43). Scientific personnel - 77 persons (43), including two Full Members of RAS (62), ten Professors (57), 34 Ph.D.s (48), 32 young scientists till 35 years (28), i.e. is 42 %.

Dynamics of the admittance to the post-graduate courses (over the years): 2000 – 5, 2001 – 4, 2002 – 7, 2003 – 4, 2004 – 4. One post-doc.

Work with the western companies

The Institute has long-term scientific relations with Universities in Germany ( Darmstadt, Bremen), the Netherlands (Wageningen), Belgium ( Leuven), Poland ( Warsaw), Portugal ( Lisbon) and The Republic of Korea ( Seoul), and also with research institutes of foreign companies, such as Bayer ( Germany), Janssen ( Belgium), Hoffmann-la-Roche ( Switzerland), Rhone- Poulenc ( France), Samsung (The Republic of Korea) and others.

Within 2000-2004 six projects financed by international funds were executed, including two INTAS Projects, one CRDF Project, two ISTC Projects, and one DFG Project; and two Contracts with PAMA Company ( Israel) and Samsung (The Republic of Korea).

Areas of Interest

Synthesis of biologically active substances, first of all, in the series of heterocyclic, fluoro-organic compounds and amino acids.

Design of new substances and materials.

Patents

On preparing the medicines, such as antibacterial drug Pefloxacine, and anticancer agent Lysomustine; and also a key intermediate in the synthesis of antibacterial Lev ofloxacine;
On preparing lubricants for the industry and all types of ski sport;
On preparing glues for metals and of the medical use;
On the methods of processing polychlorinated biphenyls;
On the methods of utilization of chromium-containing wastes aimed at preparing vitamin K3 and glyoxal;
Japan Patent JP 2000178265. Production of (S)-benzoxazine derivative and racemization of (R)-benzoxazine derivative / Chupakhin O.N., Krasnov V.P., Lev it G.L., Charushin V.N., Korolyova M.A., Tzoi E.V., Lee H.S., Park Y.J., Kim M.H., Kim K.Ch.; applicant Samsung General Chemicals Co. Ltd; publication date 27.06.2000.
Korean Patent KR 200047396. Method for preparing (S)-benzoxazine derivative and a racemization method of (R)-benzoxazine derivative / Chupakhin O.N., Krasnov V.P., Levit G.L., Charushin V.N., Korolyova M.A., Tzoi E.V., Lee H.S., Park Y.J., Kim M.H., Kim K.Ch.; applicant Samsung General Chemicals Co. Ltd; publication date 25.07.2000.
Russian Patent RU 2087458. Method of polychlorinated diphenyl chemical processing. / O.N. Chupakhin, A.Ya. Zapevalov, T.I. Gorbunova, V.I. Saloutin; publication date 20.08.1997.
Russian Patent RU 2137750. Substituted di-(formylaryl)-polyesters or their coordination compounds or their pharmaceutically acceptable additive salts, method of their synthesis and pharmaceutical composition on said. / O.N. Chupakhin, O.V. Fedorova, G.L. Rusinov, G.G. Mordovskoj, A.G. Chomenko, V.I. Golyshevskaya, M.N. Zueva, N.G. Ovchinnikova; publication date 20.09.1999.
Russian Patent RU 2168521. Method of synthesis polyfluorinated esters based on polychlorodiphenyls used as intermediate compounds for production of lubricants, antiadhesion and antifriction compositions. / A.Ya. Zapevalov, T.I. Gorbunova, V.I. Saloutin; O.N. Chupakhin, V.Ya. Bershadskij; publication date 10.06.2001.
Russian Patent RU 2175964. Method of chemical utilization (processing) of polychlorinated diphenyls. / O.N. Chupakhin, A.Ya. Zapevalov, T.I. Gorbunova, V.I. Saloutin; V.Ya. Bershadskij; publication date 20.11.2001.
European Patent EP 1081131. Selective anti-mycobacterial preparations, method for producing the same and pharmaceutical compositions / O.N. Chupakhin, O.V. Fedorova, G.L. Rusinov, G.G. Mordovskoi, A.G. Khomenko, V.I. Golyshevskaya, I.G. Ovchinnikova; publication date 07.03.2001.
Russian Patent RU 2179529. Method of preparing anhydrous manganese chloride. / Ya.N. Voitovich, O.N. Vinogradov-Zhabrov, O.N. Chupakhin, V.A. Khokhlov; publication date 20.02.02.
Russian Patent RU 2233289. Method for preparing dipeptides. / V.P. Krasnov, E.A. Zhdanova, N.Z. Solieva, I.M. Bukrina, L.Sh. Sadretdinova, M.I. Kodess, L.I. Smirnova; publication date 27.07.2004.

Histories of successes

Productions of such medicines as antibacterial “Pefloxacine” and anticancer “Lysomustine”, and also ski lubricants have been organized. Glues for metals; the Standard sample of biphenyl chlorides; Procedures for analysis of polychlorinated biphenyls, etc., are used in industry.

Publications

Books:
- Н.Д. Русьянова. Углехимия. М.: Наука, 2000. 316 с. [N .D . Rus ’yanova. Coals Chemistry. Moscow: Nauka; 2000, 316 p.].
- В.И. Салоутин, Я.В. Бургарт, О.Н. Чупахин. Фторсодержащие трикарбонильные соединения. Получение, свойства, реакции, синтез гетероциклов. Екатеринбург: УрО РАН, 2002. 242 с . [V.I. Saloutin, Ya. V. Burgart, O.N. Chupakhin. Fluorine-containing tricarbonyl compounds. Preparation, properties, reactions, synthesis of Heterocycles. Ekaterinburg: Ural Div. of RAS, 2002, 242 p.].
- Ю.Г. Ятлук. Гидридные силаны – современные реагенты для восстановления карбонильных соединений. Екатеринбург: УрО РАН, 2004. 122 с . [Yu.G. Yatluk. Hydride silans – the modern reagents for reduction of carbonyl compounds. Ekaterinburg: Ural Div. of RAS, 2004, 122 p.].
Papers:
- V.N. Charushin, O.N. Chupakhin. S N H Methodology and New Approaches to Condensed Нeterocyclic Systems. Pure Appl. Chem. 2004, v. 76 (9), 1621-1631.
- O.N. Chupakhin, G.L. Rusinov, D.G. Beresnev, V.N. Charushin, H. Neunhoeffer. A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem A N- S N ipsoand S N H- S N ipso reactions. J. Heterocyclic Chem. 2001, 901-907.
- G.L. Rusinov, D.N. Beresnev, N.A. Itsikson, O.N. Chupakhin.. Direct modification of benzoannelated crown ethers with 1,2,4-triazin-5(2H)-one moieties. Heterocycles( Japan).2001 , v. 55 (12), 2349-2359.
- O.N. Chupakhin, D.N. Beresnev. Nucleophilic attack on the unsubstituted carbon atom of azines and nitroarenes as an efficient methodology for constructing heterocyclic systems. (Review ). Russ. Chem. Rev.,2002, V . 71 (9), 707-720.
- V .N . Charushin , N .N . Mochulskaya , A .A . Andreiko , V .I . Filyakova , M .I . Kodess , O .N . Chupakhin . Aminovinyl ketones and aminovinyl esters as the C-C-N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines. Tetrahedron Lett. 2003, v. 44 (11), 2421-2424.
- S.K. Kotovskaya, V.N. Charushin, N.M. Perova, M.I. Kodess, O.N. Chupakhin. Intramolecular nucleophilic substitution of hydrogen in (quinoxalinyl-2)aminovinyl derivatives as a new approach to pyrrolo- and indolo[2,3-b]quinoxalines. Synthetic Comm. 2004, v. 34 (14), 2531-2537.
- O.N. Chupakhin, G.L. Rusinov, N.A. Itsikson, D.N. Beresnev, I.L. Nikolaeva, A.R. Burilov, A.I. Konovalov. The first case of direct coupling of heterocycles with calixarenes. Reaction of resorcinarenes with 1,2,4-triazin-5(2H)-ones. Heterocyclic Comm. 2004, v.10 (1), 14-18.
- V.P. Krasnov, G.L. Levit, V.N. Charushin, A.N. Grishakov, M.I. Kodess, V.N. Kalinin, V.A. Olshevskaya, O.N. Chupakhin. Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane. Tetrahedron: Asymmetry. 2002, V. 13, 1833-1835.
- V.P. Krasnov, G.L. Levit, I.M. Bukrina, I.N. Andreeva, L.Sh. Sadretdinova, M.A. Korolyova, M.I. Kodess, V.N. Charushin, O.N. Chupakhin. Kinetic resolution of ( ±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, ( ±)-2-methyl-1,2,3,4-tetrahydro-quinoline and ( ±)-2-methylindoline using N-tosyl-(S)-prolyl chloride. Tetrahedron: Asymmetry. 2003, V. 14, 1985-1988.
- V.P. Krasnov, G.L. Levit, M.I. Kodess, V.N. Charushin, O.N. Chupakhin. N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent in kinetic resolution of heterocyclic amines. Tetrahedron: Asymmetry. 2004, V . 15 (5), 859-862.
- V .P . Krasnov , G .L . Levit , M .A . Korolyova , I .M . Bukrina , L .Sh . Sadretdinova , I .N . Andreeva , V .N . Charushin , O.N. Chupakhin . Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine. Russ. Chem. Bull., 2004, V. 53 (6), 1253-1256.
- V.L. Rusinov, N.A.Itsikson, D.G.Beresnev, O.V.Koryakova, O.N. Chupakhin. S N H-Reactions of 1,2,4-triazines derivatives with acetophenones. Heterocyclic Comm. 2002, V. 8 (1), 75-78.
- D.N. Kozhevnikov, V.L. Rusinov, O.N. Chupakhin. 1,2,4-Tria zine N-Oxides. Advances Heterocyclic Chem. ( USA ). 2002, V. 82, 261-305.
- G.L. Rusinov , R.I. Ishmetova, I.N. Ganebnykh, O.N. Chupakhin, G.G. Aleksandrov, I.A. Litvinov, D.B. Krivolapov. Unexpected products in the reactions of s-tetrazine hydrazones with enamines. Heterocyclic Comm., 2003, V. 9 (1), 39-43.
- V.I. Saloutin, Y.V. Burgart, O.N. Chupakhin. Fluorinated аcyl(aroyl)pyruvates as the building blocks in synthesis of heterocycles. Heterocycles. 2000. V . 52 (3), 1411-1434.
- S .G . Perevalov , Ya . V . Burgart , V .I . Saloutin , O .N . Chupakhin . (Het)aroylpyruvic acids and their derivatives as promising building blocks for organic synthesis. (Review). Russ. Chem. Rev., 2001. V. 70 (11), 921-938.
- S.G. Perevalov, Y.V. Burgart, V.I. Saloutin, O.N. Chupakhin. The 4-(het)aryl-2,4-dioxobutanoic acids and their derivatives for heterocyclic syntheses. Target Heterocycl. Systems. 2001, V. 5, 419-439.
- D.L. Chizhov, D.V. Sevenard, E. Lork, K.I. Pashkevich, G.-V. Roschenthaler. Fluorinated Pd(II)-1,3,5-triketonates: synthesis and molecular structure. J. Fluorine Chem., 2004, v. 125, 1137–1141.
- D.S. Yachevskii, D.L. Chizhov, M.I. Kodess, K.I. Pashkevich. Synthesis and tautomeric equilibrium of polyfluoroacyl-containing 1,5-benzodiazepines. Monatsh. Chem., 2004, 135, 23-30.
- G.L. Levit, L.V. Anikina, Yu. B. Vikharev, A.M. Demin, V.A. Safin, T.V. Matveeva, V.P. Krasnov. Synthesis and Antiinflammatory and Analgesic Activity of Naproxen Amides with Amino Acid Derivatives. Pharm. Chem. J., 2002, V . 36 (5), 232-236.
- L.V. Anikina, G.L. Levit, A.M. Demin, Yu. B. Vikharev, V.A. Safin, T.V. Matveeva, V.P. Krasnov. Synthesis and Antiinflammatory and Analgesic Activity of Amino Acids Acylated with Ibuprofen. Pharm. Chem. J.,2002, V . 36 (5), 237-239.
- A.B . Burdin, A.L. Suvorov, L.L. Burdina, L.D. Dultzeva, T.G. Khonina, V.V. Sennikov. Study of polymers based on epoxy resins and acyloxy titanium derivatives by dielectric spectroscopy method. Plasticheckie Massy, 2001. №2, 34-36.
- L .D . Dultzeva , A .L . Suvorov , N .Yu . Ostanina , Yu .V . Shatrova , A .I . Suvorova . Physico-mechanical and dielectric properties of epoxytitaniumoxanacylate polymers. Plasticheckie Massy, 2002. № 12, 17-19.
- A .L . Suvorov , L .D . Dultzeva , N .Yu . Ostanina . Epoxytitanium-containing polymer materials. Internet Journal “Innovations”, 2003, № 4 (http://mag.innov.ru).
- V.V. Kozhukhova, Yu.G. Yatluk, A.L. Suvorov, O.V. Koryakova. Reduction of Carbonyl Compounds with Polyethylsiloxane in the Presence of Titanium Compounds. Russ. J. Org. Chem., 2004. V . 40 (6), 759-762.
- Yu .G . Yatluk , A .L . Suvorov , E .A . Khrustaleva , S .V . Chernyak . Черняк. Reaction of 2,3-Epoxypropyl Ethers with 1-Butanol. Russ. J. Org. Chem., 2004. V . 40 (6), 769-772.
- Y.A. Skorik, C.A.R. Gomes, M.T.S.D. Vasconcelos, Y.G.Yatluk. N-(2-carboxy-ethyl)chitosans: regioselective synthesis, characterization and protolytic equlibria. Carbohydrate Res., 2003, 338 (3), 271-276.
- Yu.A. Skorik, C.A.R. Gomes, M.T.S.D. Vasconcelos, Yu.G.Yatluk. Synthesis, characterization and some properties of N-(2-carboxyethyl)chitosans. Advances Chitin Sci., 2002, V.5, 344-348.
- Yu.G.Yatluk, D.V. Eremin, L.K. Neudachina, Yu.A. Skorik. Synthesis and sorption properties of new hybrid chelating sorbents with b-alanine functional groups. Russ. Chem. Bull., 2004, V .53 (12), 2730-2735.
- I .S . Amosova , E .I . Andreykov , O .N . Chupakhin . Thermal dissolution of low metamorphized coals in the presence of iron salts. Khimiya tverdogo topliva, 2003. № 3, 21-31.
- E .I . Andreykov , I .S . Amosova , O .N . Chupakhin . Thermal dissolution of rubber crumb in the organic solvents. Khimiya tverdogo topliva, 2003. № 4, 44-50.
- E .I . Andreykov , I .S. Amosova , O .N . Chupakhin . The process of thermal solvolysis of the finished-off automobile tires in goudron Internet Journal “Innovations”, 2003, № 4 (http://mag.innov.ru).
- I.S. Amosova, E.I. Andreykov, N.A. Grinevich, O.N. Chupakhin. Thermal dissolution of finished-off automobile tires in the heavy technical solvents. Chemistry for Sustainable Development. 2004. .№ 4, 431-437.
Oral presentations at the International Conferences:
- O.N. Chupakhin. Reaction of nitroazolotriazinons with N-nucleophiles. Plenary report at the 13 th International Conference on Organic Synthesis ( Poland, 2000).
- O.N. Chupakhin. Fluorinated benzofuroxanes: synthesis and ring transformations. Oral report at the 13 th European Symposium on Organic Chemistry ( Croatia, 2003).
- V.N. Charushin. New synthetic methodologies for structural modification of azaaromatics. Plenary report at the XX European Colloquium on Heterocyclic Chemistry ( Sweden, 2002).
- V.N. Charushin. New synthetic methods in the chemistry of electron-deficient arenes and hetarenes. Plenary report at the 13 th European Symposium on Organic Chemistry ( Croatia, 2003).