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Institute of Physical and Organic Chemistry at Southern Federal University
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Department of Chemistry of Heterocyclic Compounds

 Head: Professor Mezheritsky Valery V. 

Staff

Structure of the department
The staff of the department consists of 12 research associates (1 professor, 8 doctors and 3 research assistants).

The historical information
The department of chemistry of heterocyclic compounds exists from the beginning of institute (1971). The first head of a department, the Doctor of Chemistry professor G.N.Dorofeenko was the director of institute at the same time. During existence of  the department more than 300 scientific works have been published in domestic and foreign press, 6 monographies and about 20 reviews are issued, protected 5 doctor's and about 30 master's theses. Results of work were reported at numerous Russian and International conferences and symposiums. About 40 works are protected by inventor's certificates.

The basic scientific directions

  • Fine organic synthesis:  the work up the methods of synthesis, an establishment of a structure and research chemical and physical properties of monocyclic and  ortho- and peri-annelated heterocycles, nitrogenous derivatives of triazolopyrimidies, indoles and others heterocyclic compounds. 
  • Search of properties useful to practical application: synthesis of new materials with biological activity, search of dyes, luminophores, a photo, thermo- and electrofores, substances possessing chemosensoric  properties, etc.

 Contemporary subject matter of department in publications of  2007-2012 years:

  1. A.A. Spasov, D. S. Yakovlev, K. F. Suzdalev, V. A. Kosolapov, A. F. Kucheryavenko, N. A. Gurova, O. Yu. Grechko,L. V. Naumenko, N. A. Kolobrodova, T. M. Mitina, D. V. Mal'tsev,and M. N. Babakova. Synthesis and pharmacological activity of amides of 2-amino-3- indolylacrylic acid. Pharmaceutical Chemistry Journal, 2013, Vol. 46, No. 10, pp. 584-590
  2. K.F.Suzdalev, S.V. Den'Kina, G.S. Borodkin, V.V. Tkachev , M.A. Kiskin, M.E. Kletsky, O.N. Burov,  Reaction of 2-chloroindole-3-carbaldehyde with epihalogenohydrins. Tandem oxirane-opening - 1,3-oxazole-closure process , Tetrahedron, 2011, 67, p. 8775-8779.
  3. K.F. Suzdalev, S. V. Den'kina, A. A. Starikova, V.V. Dvurechensky, M.E. Kletsky, O.N. Burov. Reaction of 1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde with amines. Mendeleev Communications, 2011, 21, 231-233.
  4.  K.F.Suzdalev, S.V. Den'kina. Synthesis of sufamides of indole series. ZhurnalOrganicheskoiKhimii, 2009, Vol. 45, No. 11, pp. 1682-1684

1. S.V. Den'kina, K.F. Suzdalev. Chemistry of 3-acyl-2-haloindoles (Review). Chemistry of Heterocyclic Compounds , Vol. 48, No. 11, 2013 (Russian Original Vol. 48, No. 11, 2012).


Abstract:Methods for the synthesis and transformation of 3-acyl-2-haloindoles, which are polyfunctional reagents used for preparing various indole derivatives, are summarized. The reduction and oxidation of the acyl group, condensation at the carbonyl group, and nucleophilic and radical substitution of the halogen atom are considered. Reactions leading to [b]-fused indoles are discussed separately.

2. K.F.Suzdalev, S.V. Den'Kina, G.S. Borodkin, V.V. Tkachev , M.A. Kiskin, M.E. Kletsky, O.N. Burov,  Reaction of 2-chloroindole-3-carbaldehyde with epihalogenohydrins. Tandem oxirane-opening - 1,3-oxazole-closure process , Tetrahedron, 2011, 67, p. 8775-8779.


Abstract:Reaction of 2-chloroindole-3-carbaldehyde with epibromohydrin gives expected 1-(oxiran-2-ylmethyl) derivative. However analogous reaction with epichlorohydrin leads to the formation oxazolo[3,2-a]indole skeleton.  Some chemical properties of this tricyclic system were investigated. Its reaction with secondary amines unexpectedly proceeds with the opening of oxazole ring. 

3.  Polycyclic peri-hydroxycarbonyl compounds and their derivatives.  Mezheritskii, V.V. Russian Chemical Reviews 80 (1) , pp. 1-49 (2011)

Contents
I. Introduction 1
II. Synthetic approaches to the construction of peri-R-oxycarbonyl group 1
III. Types of interaction and conformations of peri-arranged substituents 24
IV. Chemical transformations 34
V. Natural compounds 43
VI. Conclusion

Abstract. Data on the methods of synthesis, structure and properties of polycyclic aromatic aldehydes, ketones, carboxylic acids and their derivatives containing free or substituted hydroxy or oxo group in the peri-position to the carbonyl group are generalized. The attention is focused on the intramolecular interactions between these peri-substituents and heterocyclizations involving them in comparison with heterocyclizations of similar ortho-substituted carbonyl compounds. The bibliography includes 305 references.

4. Structure of peri-hydroxy- and peri-methoxy-substituted aldehydes and ketones according to spectral data and quantum-chemical calculations. Mezheritskii, V.V., Bezuglov, A.N., Minyaeva, L.G., Lysenko, K.A., Revinskii, Yu.V., Milov, A.A. Russian Journal of Organic Chemistry 46 (1) , pp. 98-112 (2010)  

Abstract. The structure of peri-hydroxy- and peri-methoxy-substituted aldehydes and ketones of the naphthalene, acenaphthene, and acenaphthylene series and the nature of intramolecular interactions between the peri-substituents therein were determined by spectral (IR, UV, 1H NMR), X-ray diffraction, and quantum-chemical methods.

5. Peri-Annulated Heterocyclic Systems. Part I. Mezheritskii, V.V. Advances in Heterocyclic Chemistry 95 , pp. 1-25 (2007)

Abstract. The chapter presents various aspects of the chemistry of peri-fused heterocyclic systems taking into account the new findings. The chapter discusses the previously developed sequence, describing successively the compounds with larger heterocycles, with increasing number of heteroatoms in the heteroatom order N,O,S, and occasionally other heteroatoms. This chapter draws attention to the peri-fused heterocyclic naphthalene derivatives with a four-membered heterocyclic ring. Those peri-annulated heterocycles with a closed π-system that possess a double bond or another π- or p-electron "bridge" situated in the peri-position of the naphthalene ring opposite to the heterocycle should be set apart. A large number of stable representatives of four-membered heterocycles with nitrogen or oxygen ring heteroatom are described, among them also their benzoannulated derivatives. The chapter describes the peri-annulated heterocyclic naphthalene derivatives with a four-membered hetero ring- namely, (1)Naphth[1,8-bc]azete, (2)Naphtho[1,8-bc]phosphate, (3)Naphth[1,8-bc]oxete, (4)Naphtho[1,8-bc]thiete and its S-Oxides (5)Naphtho[1,8-bc]borete and (6)Naphtho[1,8-bc]silete.

Some monografs and revives of previous times
  1. ”Pyrylium salts. Sy nthesis, reactions and physical properties”, Adv. Heterocyclic Chemistry, Acad. Press, New-York, 434 pages, 1982.A.T. Balaban, A. Dinculescu, G.N.Dorifeenko, G.W.Fischer, A.V. Koblik,  V.V.Mezheritskii, and W.Schrot (monography).
  2. V.V.Mezheritskii, A.L.Pikus, G.N.Dorofeenko. Reactions of α- and γ-alkyl groups in pyrylium salts.”Hetero-cycles”, v.12, N1, p. 51-93, 1979
  3. V.V.Mezheritskii, V.V.Tkachenko. Synthesis of peri-annelated heterocyclic systems. Adv. Heterocyclic Chemistry. Academic Press, New-York, v. 51, p. 1-103, 1991
  4. Yu.I.Ryabukhin, O.B.Korzhavina, K.F.Suzdalev. Chemistry of 1,3-Thiazine-4-ones and Their Derivatives, Advances in Heterocyclic Chemistry, Academic Press, New-York, vol. 66, pp. 131 - 191, 1996.
  5. V.V.Mezheritskii. Peri-annulated heterocyclic systems. Part I. Peri-annulated heterocyclic naphthalene derivatives with a four-membered heteroring.  Adv. Heterocyclic Chemistry. Academic Press, New-York, 2007

Some publications of previous times (2000-2006):

  1. V.V.Mezheritskii, R.V.Tyurin, and L.G..Minyaeva. Synthesis of 4,8-Dibenzoyl-1,5-dihydroxynaphthalene and  of Some Derivatives Thereof. Russian Journal of Organic Chemistry, Vol.37, No.4, 2001, pp. 513-516.
  2. S.N.Chuprakov, R.V. Tyurin, L.G. Minyaeva, L.V. Mezheritskaya, and V.V.Mezheritskii. Synthesis of 2-(3,3-Dicyano-2-propenylidene)-4,4,5,5-tetramethyl-dioxolane and Its Reactions with Hydrazine and Primary Amines. Russian Journal of Organic Chemistry, Vol. 39, No. 7, 2003, pp. 1016-1020.
  3. R.V. Tyurin, L.G. Minyaeva, and V.V. Mezheritskii. A new procedure for fusion of a five-membered ring. Building up of the naphtha[1,8-bc]furan system. Russian Journal of Organic Chemistry,  Vol. 40, No.9, 2004, pp. 1300-1302.
  4. V.V.Mezheritskii, V.I. Minkin, L.G. Minyaeva, R.V. Tyurin, V.V. Krasnikov, E.V. Vorobyev, and Z.A. Starikova. Two approaches to a new hetercyclic system of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine. ARKIVOC(e-journal), Vol. 2005, 2004, pp. 9-17.
  5. R.V. Tyurin, A.N. Antonov, L.G.Minyaeva, and V.V. Mezheritskii. Specific Character of the Pechman Reaction of 4,8-Di-tert-butyl-5-hydroxy-2-(4-methoxyphenyl)-2H-naphtho[1,8-bc]furan with Ethyl Acetoacetate . Russian Journal of Organic Chemistry, Vol 40, No. 12, 2004, pp. 1828-1829.
  6. R.V. Tyurin, A.N. Antonov, L.G..Minyaeva, and V.V. Mezheritskii. Building up of a peri-Hydroxynaphthoyl Fragment on the Core of 2H-Naphtho[1,8-bc]furan. Russian Journal of Organic Chemistry, Vol 41, No. 2, 2005,  pp. 1828-1829.
  7. V.V.Mezheritskii,  L.G. Minyaeva, and R.V. Tyurin. Synthesis of new 1H-pyridazine derivatives peri-annelated with acenaphthene and acenaphthylene.  Russian Chemical Bulletin, International Edition, Vol. 54, No. 3, 2005, pp. 792-795.
  8. R.V. Tyurin, E.V.Vorob’ev, L.G..Minyaeva, V.V. Krasnikov, and  V.V. Mezheritskii. Alternative Routs to the Pyrazolo[4,3-e][1,2,4]triazolo [1,5-c]pyrimidine System. Russian Journal of Organic Chemistry, Vol 41, No. 6, 2005,  pp. 916-921
  9. V.V.Mezheritskii, L.G. Minyaeva, O.M.Goyanskaya, R.V. Tyurin, O.Ya. Borbulevich, G.S.Borodkin, and A.N. Antonov. Oxidative Transformations of Peridazines. Russian Journal of Organic Chemistry, Vol  42, No. 2, 2006,  pp. 278-287
  10. E.S.Kurbatov, V.V. Krasnikov, and  V.V. Mezheritskii. Bicyclic ortho-Aminocarbonitriles – New Accessible Synthons. Russian Journal of Organic Chemistry, Vol 44, No. 3,  2006,  pp. 460-462.
  11. N.M.Vlaskina,.K.F. Suzdalev, M.N. Babakova, V.V.Mezheritskii, and V.G. Kartsev. Use of the tert-amino effect in the synthesis of spirocyclic fused α-carbolines. Russian Chemical Bulletin, International Edition, Vol. 55, No.2, pp. 384-386
  12. E.V.Vorob’ev, E.S.Kurbatov, V.V. Krasnikov, and  V.V. Mezheritskii, and
    E. V. Usova. Synthesis and rearrangements of 7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]- and 7H-pyrrolo[3,2-e]]1,2,4]triazolo[4,3-c]pyrimidines.  Russian Chemical Bulletin, International Edition, Vol. 55, No.8, pp. 1492-1497.
  13. E.S.Kurbatov, Z.A.Starikova, V.V.Krasnikov, and V.V.Mezheritskii. Synthesis of benzopyranotriazolopyrymidine spirofuzed with an oxindole fragment. Chemistry of Heterocyclic Compounds. Vol. 42, No 10, pp. 1366-1367, 2006.
  14. V.V. Mezheritskii,  R.V. Tyurin, L.G..Minyaeva A.N. Antonov, , and A.P.Zadopozhnaya. Reaction of Naphthalene-1,5-diol and its Derivatives with β-Dicarbonyl and α,β-Unsaturated Carbonyl Compounds . Russian Journal of Organic Chemistry, 2006. Vol. 42, No.10,  pp. 1458-1463
  15. E.S.Kurbatov, Z.A.Starikova, V.V.Krasnikov, and V.V.Mezheritskii. New Method for Functionalization of 6’-Amino-3’-methyl-2-oxo-1’-phenyl-1,2-dihydro-1’H-spiro[indole-3,4’-pyrano-[2,3-c]pyrazole]-5’-carbonitrile. Russian Journal of Organic Chemistry, 2006. Vol. 42, No.10,  pp. 1578-1580.

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