Laboratory of Organochalcogen Compounds

History of the lab

The laboratory of organochalcogen compounds was founded in January, 1986 on the basis of a group separated from laboratory of unsaturated heteroatomic compounds. From that date till 2018 the lab was headed by Prof. S.V. Amosova. From 2018 the head of laboratory is Prof. V.A. Potapov.

Vladimir A. Potapov, Dr.Sc., Professor, the head of the laboratory. After graduation with excellence from the Irkutsk State University in 1980, he is working in the A. E. Favorsky Irkutsk Institute of Chemistry. In 1983 he defended the Ph.D. thesis entitled „Reactions of selenium with acetylene: a route to unsaturated and functional organoselenium compounds (research supervisors: Academician B.A. Trofimov and Professor N.K. Gusarova). In 1993 he defended the Dr.Sc. thesis entitled „New methods for the synthesis of organoselenium -tellurium compounds on the basis of organic dichalcogenides and elemental chalcogens”. In 2000 he was appointed to a professorship. He is a research supervisor of 11 Ph.D. theses. He is the author of more than 200 papers and reviews in leading domestic and foreign journals.

Staff

20 employees (10 researchers) including 3 Dr. Sc., 9 Ph.D., 2 Ph.D. students.

Alexander V. Martynov, Dr.Sc., leading researcher, the head of a group. In 1980 he defended the Ph.D. thesis entitled „Investigations into the reactions of chloroethylenes thiylation and properties of organyl(chlorovinyl)sulfides and sulfones” (research supervisors: Academician M.G. Voronkov and Ph.D. A.N. Mirskova). In 2007 he defended the Dr.Sc. thesis entitled dissertation „Halovinylchalcogenides and bis(organylchalcogeno)acetylenes: new methods of synthesis from polyhaloethenes, haloacetylenes and diethynylsilanes”. In 1993 he was appointed to senior researcher. He is the author of more than 100 papers and reviews in leading domestic and foreign journals.

Areas of research

· A fundamental approach to the synthesis of organochalcogen compounds from chalcogen halides including selenium dichloride and dibromide is developed. These new electrophilic reagents, introduced for the first time in organic synthesis by the laboratory of organochalcogen compounds, allow implementing a wide series of chemo-, regio- and stereoselective reactions to afford precursors of innovative highly efficient materials for micro- and nanoelectronics and potentially biologically active agents.

· The chemistry of divinyl chalcogenides (divinyl sulfide, divinyl selenide, divinyl telluride) and their analogs and derivatives, unique building blocks of organochalcogen compounds, semi-products and synthons of organic synthesis, is elaborated.

· A fundamental effect of anchimeric assistance of chalcogen atoms in new reactions and rearrangements is studied. Methods for the synthesis of novel classes of unsaturated sulfur- and selenium-containing compounds possessing potential biological activity, including those with glutationperoxidase-like effect, are developed. The methods are based on new rearrangements of chalcogen-containing heterocyclic systems with opening, narrowing or expansion of the cycle.

· Novel methods for heterocyclization and annelation of chalcogen-containing heterocyclic systems using new reagents (selenium dihalides) via sigmatropic rearrangements are developed to produce new conducting materials and biologically active substances.

· The processes and technologies which may find application in industry are worked out. Methods for the preparation of important polyunsaturated hydrocarbons via the cross-coupling of acetylene and its derivatives with halogen-containing compounds using inexpensive available catalysts (palladium-free) are developed.

· Novel regio- and stereoselective fundamental approaches to practically valuable chalcogen-containing compounds are elaborated. The methods involve generation of highly reactive nucleophilic reagents from elemental chalcogens or organic dichalcogenides and their introduction to the reactions of nucleophilic addition and substitution.

· Earlier unknown reactions of tellurium tetrahalides with acetylenes and alkenes are investigated. Stereo- and the regioselective methods for the synthesis of new organotellurium compounds, promising semi-products for organic chemistry and reagents for microelectronics, are developed on the basis of these reactions

· Novel organochalcogen-based drugs are designed. Highly effective anti-tuberculosis medicine Perkhlozon is introduced into practice. Direct synthesis of analogs and derivatives of Perkhlozon, Ebselen and AS-101 drugs is implemented to design new biologically active compounds.

Principal results

The first application of selenium dichloride and dibromide in the synthesis of organoselenium compounds (Scheme 1)

It is a common knowledge that selenium dichloride and dibromide cannot be isolated as individual compounds and in solution they undergo disproportionation. Using the reaction with dimethyldiethylsilane as an example, it has been shown for the first time that selenium dichloride and dibromide generated in situ can be employed in the synthesis of organoselenium compounds. The addition of selenium dichloride and dibromide to dimethyldiethylsilane delivers hitherto unknown 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes (Scheme 1).

Scheme 1.

V.A. Potapov, S.V. Amosova, A.G. Yarosh, M.G. Voronkov, Synthesis of 3,6-dihalo-4,4-dimethyl-1,4-selenasilafulvenes // Chem. Heterocycl. Compd. — 2003. — Vol. 39, No 4. — P. 549-550.

V.A.Potapov, S.V.Amosova, New methods for the synthesis of organoselenium and —tellurium compounds from elemental chalcogens // Russ. J. Org. Chem. — 2003. — Vol. 39, No 10. — P. 1373-1380.

Development of fundamental chemistry of divinyl chalcogenides: divinyl sulfide, divinyl selenide, divinyl telluride, their analogs and derivatives (Scheme 2)

Scheme 2.

S.V. Amosova, M.V. Penzik, A.I. Albanov, V.A. Potapov. Addition of selenium dibromide to divinyl sulfide: spontaneous rearrangement of 2,6-dibromo-1,4-thiaselenane to 5-bromo-2-bromomethyl-1,3-thiaselenolane // Tetrahedron Lett. — 2009. — Vol. 50, No 3. — P. 306-308.

S.V.Amosova, M.V.Penzik, A.I.Albanov, V.A.Potapov. The reaction of selenium dichloride with divinyl sulfide // J. Organomet. Chem. — 2009. — Vol. 694, No 20. — P. 3369-3372.

V.A.Potapov, V.A.Shagun, M.V.Penzik, S.V.Amosova. Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results // J. Organomet. Chem. — 2010. — Vol. 695, No 10-11. — P. 1603-1608.

V.A.Potapov, S.V.Amosova, K.A.Volkova, M.V.Penzik, A.I.Albanov. Reactions of selenium dichloride and dibromide with divinyl selenide: synthesis of novel selenium heterocycles and rearrangement of 2,6-dihalo-1,4-diselenanes // Tetrahedron Lett. — 2010. — Vol. 51, No 1. — P. 89-92.

Systematic investigations of chemical behavior of new reagents, selenium dichloride and dibromide, in the reactions with diverse compounds containing the double bond.

Fundamental investigations of chemical behavior of new reagents, selenium dichloride and dibromide, in the reactions with diverse compounds containing the double bond, are carried out. Te effect of the reaction conditions, reagents ratio, electron-donating and electron-withdrawing substituents in alkene and halogen nature on chemo-, regio- and stereoselectivity of the process and the products yield is elucidated. It has been found that the reactions of selenium dihalides with simplest terminal alkenes and the compounds bearing the vinyloxy group (alkylvinyl ethers, vinyl acetate), vinylsulfanyl and cinylselanyl moieties (vinyl sulfides, vinyl selenides) furnish the Markovnikov adducts in high or quantitative yields. When a strong electron-withdrawing substituent (carbonyl, sulfone, sulfoxide groups) is contained at the double bond, the anti-Markovnikov adducts are exclusively or predominantly formed (addition of selenium dihalides to divinyl sulfone, Scheme 3), i.e. vinyl methyl ketone, acrylic acid and its ether, acrilonitrile, etc.

Scheme 3.

Potapov V.A., Kurkutov E.O., Musalov M.V., Amosova S.V. Reactions of selenium dichloride and dibromide with divinyl sulfone: synthesis of novel four- and five-membered selenium heterocycles // Tetrahedron Lett. — 2010. — Vol. 51. N 40. — P. 5258-5261.

The reaction of transannular addition of selenium dihalides to cyclooctatetraene leading to 2,6-dihalo-9-selenabicyclo[3.3.1]nonanes has been accomplished for the first time (Scheme 4). Structure of products has been proved by the X-ray diffraction analysis (Fig. 1).

Scheme 4.

Fig. 1. Packing of molecules in crystal

Accurso A.A., Cho S-H., Amin A., Potapov V.A., Amosova S.V.,Finn M.G. Thia-, Aza-, and Selena [3.3.1] bicyclononane Dichlorides: Rates vs Internal Nucleophile in Anchimeric Assistance // J. Org. Chem. — 2011. — Vol. 76, No.11. — P. 4392-4395.

In the case of diallylic ether, diallyl sulfide and diallyl selenide, the reaction furnishes the anti-Markovnikov adducts, 3,5-bis(halomethyl)-1,4-chalcogenoselenanes. Regioselectivity of the addition may be rationalized by the fact that 6-membered heterocycles are thermodynamically more favorable than possible 8-membered heterocycles (the Markovnikov adducts). Straightforward methods for the synthesis of 3,5-bis(halomethyl)-1,4-oxaselenanes, 3,5-bis(halomethyl)-1,4-thiaselenanes and 3,5-bis(halomethyl)-1,4-diselenanes are elaborated on the basis of these reactions (Scheme 5).

Scheme 5.

Potapov V.A., Musalov M.V., Abramova E.V., Musalova M.V., Rusakov Yu.Yu., Amosova S.V. Efficient method for the synthesis of 3,5-bis(halomethyl)-1,4-oxaselenanes and their derivatives // Chem. Heterocycl. Compd., — 2013, — № 12. — P. 1965-1971.

Musalov M.V., Volkova K.A., Potapov V.A., Albanov A.I., Amosova S.V. Regioselective reaction of selenium dibromide and dichloride with diallyl sulfide // Russ. J. Org. Chem. — 2012. — Vol. 48. — No 12. — P. 1580-1581.

Potapov V.A., Amosova S.V., Volkova K.A., Musalov M.V., Albanov A.I. Synthesis of 2,6-bis(chloromethyl)-1,4-diselenane // Russ. Chem. Bull., Int. Ed. — 2011. — Vol. 60, — No 12. — P. 2128-2129.

Development of efficient methods for the synthesis of unsaturated organoselenium compounds via the reaction of selenium dichloride and dibromide with acetylene and its derivatives

The reactions of selenium dichloride and dibromide with acetylene have been carried out for the first time. The reactions proceed as stereoselective anti-addition giving rise to earlier unknown E,E-bis(2-chlorovinyl)selenide and E,E-bis(2-bromovinyl)selenide in 98-99% yields (Scheme 6).

Scheme 6.

Musalov M.V., Potapov V.A., Musalova M.V., Amosova S.V. Stereospecific synthesis of  (Е, E)-bis(2halovinyl) selenides and its derivatives based on selenium halides and acetylene // Tetrahedron — 2012. —Vol 68, — No 51. — P 10567-10572.

Potapov V.A., Khuriganova O.A., Musalov M.V., Larina L.I., Amosova S.V. Stereospecific synthesis of E,E-bis(2-chlorovinyl) selenide // Russ. J. Gen. Chem. — 2010. — Vol. 80. — No 3. — p. 541-542.

Potapov V.A., Musalov M.V., Khuriganova O.A., Larina L.I., Amosova S.V. Reactions of stereospecific addition of selenium dibromide and monobromide to acetylene // Russ. J. Org. Chem. — 2010. — Vol. 46, — No 5. — p. 753-754.

Expedient methods for the synthesis of novel heterocyclic systems are developed on the basis of addition of selenium dichloride and dibromide to diethynylsilanes and diethynylgermanes (Scheme 7).

Scheme 7.

Amosova S.V., Martynov A.V., Mahaeva N.A., Belozerova O.A., Penzik M.A., Albanov A.I., Yarosh O.G., Voronkov M.G. Unsaturated five-membered selenium-silicon containing heterocycles based on the reactions of selenium di- and tetrahalides with diorganyl diethynyl silanes // J. Organomet. Chem.— 2007. — Vol. 692, — No 5. — P. 946-952.

Amosova S.V., Penzik M.V., Martynov A.V., Makhaeva N.A., Yarosh N.O., Voronkov M.G. Unsaturated five-membered selenium-germanium containing heterocycles based on the reactions of selenium di- and tetrahalides with diorganyl diethynyl germanes // J. Organomet. Chem. — 2008. — Vol. 693, — No 21-22.— P. 3346–3350.

Fundamental approach to the synthesis of important unsaturated organic compounds via cross-coupling of acetylene and its derivatives.

The efficient methods for the preparation of allylacetylene (80% yield) and diallylacetylene (72%) have been developed. The methods comprise cross-coupling of acetylene with allyl halides under atmospheric pressure in the presence of copper halides, basis and reducing agent (Scheme 8). Allyl- and diallylacetylenes are absent in chemical catalogs of leading foreign companies. However, these compounds are very promising semi-products for the organic synthesis since they contain double and triple bond which is prone to participate in the addition reaction. The application of these compounds was so far limited due to the lack of convenient protocols of their synthesis. The above methods using acetylene under atmospheric pressure make these products easily available.

Possibilities of novel heterocycles functionalization via the involvement of halogen endocyclic atoms to the reactions of nucleophilic substitution and cross-coupling with terminal acetylenes are studied (Scheme 9).

Scheme 8.

Potapov V.A., Musalov M.V., Panov V.A., Musalova M.V., Amosova S.V. Allylation of acetylene under atmospheric pressure // Russ. J. Org. Chem. — 2013. — Vol. 49. — No 12. — p. 1834-1835.

Musalov M.V., Musalova M.V., Potapov V.A., Amosova S.V. Method for the preparation of 1-penten-4-yne by CuI-catalyzed reaction of acetylene with allyl bromide // Russ. Chem. Bull., Int. Ed. — 2012. — Vol. 61, — No 10. — p. 2007-2008.

Scheme 9.

Martynov A.V., Makhaeva N.A., Larina L.I., Amosova S.V. Bis-E-chloromethylydene derivatives of 4-thio- and 4-selenomorpholineamines // Chem. Heterocycl. Compd. — 2012. — Vol. 48, — No 9. — p. 1425-1427.

Martynov A.V., Larina L.I., Amosova S.V. Nove bis[(E)-1-(halomethyl)-2-chlorovinyl] chalcogenides as starting material for the efficient synthesis of bis(chloromethylidene)-1,4-dichalcogenanes // Tetrahedron Lett. — 2012. — Vol. 53, — No 10. — P. 1218-1221.

Martynov A.V., Amosova S.V. Cross-coupling of 2,6-bis(chloromethylydene)-1,4-dithiane with phenylacetylene as an example of synthesis of symmetric bridge bis-enyne compounds // Russ. J. Org. Chem. — 2013. — Vol. 49, — No 11. — p. 1720-1721.

Fundamental effect of anchiomeric assistance of chalcogen atoms. Development of methods for the synthesis of new valuable products via earlier unknown rearrangements of chalcogen-containing heterocyclic systems with opening, narrowing or expansion of the cycle and reactions of nucleophilic substitution.

The kinetic studies have shown that the anchimeric effect of selenium atom is by the order higher than that of sulfur and nitrogen atoms. 2,6-Dihalo-9-selenabicyclo[3.3.1]nonanes and their sulfur- and nitrogen-containing analogs are used in these researches as model compounds (Scheme 10).

Scheme 10.

Accurso A.A., Cho S.-H., Amin A., Potapov V.A., Amosova S.V., Finn M.G. Thia-, Aza-, and Selena [3.3.1]bicyclononane Dichlorides: Rates vs Internal Nucleophile in Anchimeric Assistance // J. Org. Chem. — 2011. — Vol. 76,  — No. 11. — P. 4392-4395.

A one-pot method for the synthesis of 2-bromomethyl-1,3-thiaselenole (in 95% yield) via the reaction of divinyl sulfide with selenium dibromide at room temperature has been developed. The selenium dibromide imparts unusual properties to the heterocycle due to anchimeric effect of selenium atom. 2-Bromomethyl-1,3-thiaselenole shows unexpected reactivity in the reactions with diverse nucleophiles and bases (Scheme 11). For instance, reactions with alkoxide- and carboxylate-anions lead to new rearrangements involving the cycle expansion to afford hitherto unknown 2-substituted 2,3-dihydro-1,4-thiaselenines, while the reaction with thiolate-anions proceeds unexpectedly and is accompanied by opening the cycle to stereoselectively give new class of unsaturated selanyl sulfides of the Z-configuration. The selective dehydrobromination leading to 2-methyl-1,3-thiaselenole or 1,4-thiaselenine and elimination of selenium dibromide resulting in Z,Z-di[2-(vinylsulfanyl)ethenyl]selenide is accomplished.

Scheme 11.

Amosova S.V., Penzik M.V., Potapov V.A., Albanov A.I. Synthesis of 2,6-dichloro-1,4-dithiane. Effect of chalcogen nature on stability of 2,6-dichloro-1,4-thiachalcogenanes // Chem. Heterocycl. Compd. — 2012. — Vol. 48, — No 11. — P. 1716-1718.

Amosova S.V., Penzik M.V., Potapov V.A., Albanov A.I. Unexpected reaction of 2-bromomethyl-1,3-thiaselenole with carboxylic acid salts // Russ. J. Org. Chem. — 2014. — Vol. 50.  — No 1. — p. 152-154.

New methods for heterocyclization and annelation of organochalcogen compounds. Synthesis of new heterocyclic systems, potential biologically active substances and conducting materials.

Methods for the annelation of organochalcogen compounds are developed. The methods combine the addition reactions of selenium dihalides and electrophilic aromatic substitution. For example, a method for the annulation of 2,3-dihydro-1,4-benzoxaselenine to the benzene ring to deliver 3-chloromethyl-2,3-dihydro-1,4-benzoxaselenine and E-3-chloromethylene-2,3-dihydro-1,4-benzoxaselenine in up to 98% yields has been elaborated on the basis of the reaction of selenium dichloride with allylphenyl and propargylphenyl ethers (Scheme 12).

Scheme 12.

Methods for annelation of organochalcogen compounds through [3,3]-sigmatropic rearrangements of the heterocycles containing propargylchalcogenyl group are developed. The annelation of the thiazole ring via the reactions of benzimidazole-2-thione derivatives, 2-propargylsulfanylbenzimidazole and 2-allenylsulfanylbenzimidazole, is systematically studied. Expedient methods for the synthesis of 2-methylthiazole[3,2-a][1,3]benzimidazole and 3-methylthiazole[3,2-a][1,3]benzimidazole (Scheme 13) are elaborated. Structure of the reaction products is proved by X-ray diffraction analysis data (Fig. 2).

Scheme 13.

Fig. 2. X-ray diffraction analysis data for 2-methylthiazole[3,2-a][1,3]benzimidazole and 3-methylthiazole[3,2-a][1,3]benzimidazole

Potapov V.A., Musalov M.V., Amosova S.V. Reactions of selenium dichloride and dibromide with unsaturated ethers. Annulation of 2,3-dihydro-1,4-oxaselenine to the benzene ring // Tetrahedron Lett. — 2011. — Vol. 52, No 36. — P. 4606-4610.

Potapov V.A., Malinovich D.A., Amosova S.V., Bhasin K.K. Annelation of 8-propargylsulfanylquinoline // Chem. Heterocycl. Comp. — 2012. — Vol. 48, — No 7. — P. 1127-1128.

Musalov M.V., Potapov V.A., Amosova S.V. Annelation of propargyl phenyl ether with selenium dichloride // Russ. Chem. Bull., Int. Ed. — 2011. Vol. 60, — No 4. — p. 767-768.

Musalov M.V., Potapov V.A., Amosova S.V. Reaction of selenium dichloride with allyl phenyl ether // Russ. J. Org. Chem. — 2011. — Vol. 4. — No 6. — p. 948-949.

Development of stereo- and regioselective methods for the synthesis of earlier unknown organotellurium compounds, promising semi-products for organic synthesis and reagents for microelectronics, via the reactions of tellurium halides with acetylene, its derivatives and alkenes.

The reactions of tellurium tetrachloride and tetrabromide with acetylene have been carried out and systematically studied for the first time. It is found that the reactions proceed stereospecifically as anti-addition to deliver the products of the E-configuration, unknown earlier E-(2-halovinyl)tellurium trihalides and E,E-bis(2-halovinyl)tellurium dihalides. The conditions allowing to selectively obtain either monoadducts, E-(2-halovinyl)telluriumtrihalides, or bis-adducts, E,E-bis(2-halovinyl)tellurium dihalides, are found (Scheme 14). A possibility of these compounds synthesis under atmospheric pressure of acetylene is shown.

Scheme 14.

The reactions represent a first example of stereoselective anti-addition of tellurium tetrachloride and tetrabromide to the triple bond of acetylenic hydrocarbons.

Musalova M.V., Potapov V.A., Amosova S.V. Synthesis of Novel E-2-Chlorovinyltellurium Compounds Based on The Stereospecific anti-Addition of Tellurium Tetrachloride to Acetylene // Molecules. — 2012. — Vol. 17, — No 5. — P. 5770-5779.

Potapov V.A., Musalova M.V., Amosova S.V. Synthesis of Е-2-chlorovinyltellurium trichloride and Е,Е-bis(2-chlorovinyl)ditelluride // Russ. Chem. Bull., Int. Ed. — 2012. — Vol. 61, No 1. — p. 204-205.

Musalova M.V., Potapov V.A., Musalov M.V., Amosova S.V. Stereoselective synthesis of Е-(2-bromovinyl)tellurium tribromide // Russ. J. Org. Chem. — 2011. — Vol. 47, — No 6. — p. 1397-1398.

New highly effective antituberculosis drug of new generation Perchlozon^â has been created (research supervisor is Academician B.A. Trofimov) (together with pharmaceutical company „Farmasintez” and St.-Petersburg research institute of phthisiopulmonology).

Perkhlozon is the only original highly effective antituberculosis drug created in the world over the last 40 years. The prime minister of the Russian Federation D.A. Medvedev called Perkhlozon one of two „breakthrough” Russian medicines. In November, 2012 Perkhlozon was registered (No. LP-001899 of 09.11.12) as a medicine and approved for application in clinics. In December, 2012 industrial production of Perkhlozon was launched by pharmaceutical company „Farmasintez”. It is planned that in 2014-2015 the production of Perchlozon will be scaled up to satisfy the demands of domestic market (Fig. 3).

The long-term program of joint investigations of the institute and „Farmasintez” in the field of design of new drugs has been adopted. In the framework of this program the joint research is focused to search and development of new antituberculosis, anticancer and anti-HIV medicines.

Fig. 3. The container of Perchlozon drug produced in December, 2012.

Prize of International Academic Publishing Company „Nauka” (MAIK)

Prize of International Academic Publishing Company „Nauka” (MAIK) was awarded to S.V. Amosova, V.A. Potapov, A.V. Martynov, M.V. Musalov, M.V. Penzik, M.V. Musalova, N.A. Makhayeva, and A.G. Khabibulina for the best papers related to „Development of efficient region- and stereoselective methods for the synthesis of new organochalcogen compounds via the reactions of chalcogen halides as well as novel electrophilic reagents, selenium dihalides, introduced into organic synthesis for the first time” published in „Russian Journal of Organic Chemistry” in 2012.

MAIK Prize winners

Main Articles (2015-2018)

1. Potapov V.A., Amosova S.V., Abramova E.V., Lyssenko, K.A., Musalov M.V., Finn M.G. Transannular Addition of Selenium Dichloride and Dibromide to 1,5-Cyclooctadiene: Synthesis of 2,6-Dihalo-9-selenabicyclo[3.3.1]nonanes and Their Complexes with Selenium Dihalides // New J. Chem. - 2015. - V.39, No.10. - P.8055-8059. DOI: 10.1039/C5NJ00684H.

2. Potapov V.A., Musalova M.V., Ishigeev R.S., Musalov M.V., Panov V.A., Khabibulina A.G., Amosova S.V., Bhasin K.K. Efficient and selective syntheses of novel unsaturated chalcogen-containing pyridine derivatives // Tetrahedron Lett. - 2016. - V. 57, N 48. -P. 5341-5343.

3. Amosova S.V., Novokshonova I.A., Penzik M.V., Filippov A.S., Albanov A.I., Potapov V.A. Reaction of 2-bromomethyl-1,3-thiaselenole with thiourea: en route to the first representatives of 2-(organylsulfanyl)-2,3-dihydro-1,4-thiaselenines // Tetrahedron Lett. - 2017. - V.58, No. 46. - P.4381-4383. DOI: 10.1016/j.tetlet.2017.10.011.

4. Potapov V.A., Musalov M.V., Musalova M.V., Amosova S.V. Recent Advances in Organochalcogen Synthesis Based on Reactions of Chalcogen Halides with Alkynes and Alkene // Curr. Org. Chem. - 2016. - V. 20, N 2. - P. 136-145.

5. Abramova E.V., Sterkhova I.V., Molokeev M.S., Potapov V.A., Amosova S.V. First coordination compounds of SeBr2 with selenium ligands: X-ray structural determination // Mendeleev Communications. - 2016. - V. 26, N 6. - P. 532-534. DOI: 10.1016/j.mencom.2016.11.025.

6. Chirkina E.A., Chernyshev K.A., Pankratiev E.Yu., Krivdin L.B., Potapov V.A., Amosova S.V. Quantum-chemical study of organic reaction mechanisms. Part 2. Addition of selenium dichloride to acetylene // J. Organomet. Chem. - 2014. - V. 766. - P. 49-56. DOI: 10.1016/j.jorganchem.2014.04.036.

7. Amosova S.V., Penzik M.V., Potapov V.A., Filippov A.S., Shagun V.A., Albanov A.I., Borodina T.N., Smirnov V.I. Unexpected Regioselective Reactions of 2-Bromomethyl-1,3-Thiaselenole with Dithiocarbamates. The First Example of Nucleophilic Attack at Selenium Atom of Seleniranium Intermediate // SynLett. - 2016. - V. 27, N 11. - P. 1653-1658.

8. Martynov A.V., Makhaeva N.A., Amosova S.V. (2E,6E)-2,6-Bis(organylchalogenylmethylidene) substituted 1,4-dithiane 1,1,4,4-tetraoxides and N-organyl thiomorpholine 1-oxides as new S-oxide derivatives of bis(2-organylchalcogenylvinyl) sulfides // Heteroatom Chemistry. - 2018. - V. 29. - P. e21420 (1-7). DOI: 10.1002/hc.21420.

9. Potapov V.A., Musalov M.V., Musalova M.V., Rusakov Yu.Yu., Khabibulina A.G., Rusakova I.L., Amosova S.V. Stereoselective synthesis of E-2-halovinyl tellanes, ditellanes and selenides based on tellurium tetrahalides, selenium dihalides and internal alkynes // Journal of Organometallic Chemistry. - 2018. - V. 867. - P. 300-305. DOI: 10.1016/j.jorganchem.2018.02.015.

10. Amosova S.V., Rykunova Yu.I., Filippov A.S., Penzik M.V., Makhaeva N.A., Albanov A.I., Potapov V.A. Cascade regio- and stereoselective reactions of 2-bromomethyl-1,3-thiaselenole with water and ethylene glycol: En roote to the first representatives of polyfunctional 2,3-dihydro-1,4-thiaselenines // Journal of Organometallic Chemistry. - 2018. - V. 867. - P. 398-403. DOI: 10.1016/j.jorganchem.2018.03.037.

Grants and contracts in 2014

I. Grants of Russian Foundation of Basic Research

Heads of RFBR grants

RFBR_12-03-01098_a „Selenium dichloride and dibromide as new effective and selective reagents for organic synthesis” (Head — Professor Potapov V.A.).

RFBR_13-03-00400_a „New direction in selenium dihalides chemistry. Anchimeric effect of selenium atom in cyclic adducts of selenium dihalides as a driving force of new rearrangements with the cycle expansion and stereospecific reactions of the cycle opening to form new classes unsaturated functionalized organoselenium compounds and heterocycles” (Head — Professor Amosova S.V.).

RFBR_14-03-00185_a „New tellurium-containing organic heterocycles on the basis of adducts from electrophilic reactions of tellurium tetrahalides with propargylhalides” (Head — Dr. Sc. Martynov A.V.).

RFBR_14-03-31939_mol_a: „Development of methods for the synthesis of new classes unsaturated sulfurselenium-containing functionalized compounds via novel regio- and stereoselective reactions and rearrangements of 2-bromomethyl-1,3-thiaselenole” (Head — Ph.D. Penzik M.V.).

RFBR_14-03-31910_mol_a: „Cross-coupling of acetylene and its derivatives: development of fundamental approach to the synthesis of valuable unsaturated compounds, their reactions with selenium dihalides, selenides and alkali metal organylselenolates” (2014-2015, Head — Ph.D. M. V. Musalov).

RFBR_No. 14-03-31911_mol_a: „Development regio- and stereospecific methods for the preparation of new organotellurium compounds containing Z- and E-2-halovinyl groups, and their application in stereoselective synthesis of alkenes” (2014-2015, Head — Ph.D. M.V. Musalova).

Program of basic researches of Presidium of the Russian Academy of Sciences, Project 8.16: „New methodology of introduction of selenium atom into organic molecule on the basis of selenium dihalides. Synthesis of fundamentally new classes the selenium-containing heterocycles, promising building blocks for the preparation of organic electroconducting materials of new generation” (Head — Professor Amosova S.V.).

Program of basic researches of the department of chemistry and material science of the Russian Academy of Sciences No. 5.1.8: „Study of anchimeric effect of chalcogen atoms for the development of new methods for functionalization of organochalcogen compounds” (Head — Professor Potapov V.A.).

Contract with pharmaceutical company „Farmasintez”: „Synthesis of potential biologically active agents for studying the antituberculosis, anticancer and immunomodulating activity”. (Head — Academician B.A. Trofimov, 2013-2014).