Leninsky Prospect, 47, Moscow
Phone: +7 499 137-29-44
Fax: +7 499 135-53-28

Laboratory of Chemistry of Heterofunctional Compounds (N25)

Head: Anatoly M. Shestopalov, Prof., DSc in Chemistry (e-mail: amshioc.ac.ru, tel. +7 (499)135-8804)

The laboratory was organized in 1986 by Professor V.P. Litvinov on the basis of former Laboratory of Herbicides headed by Professor E.N. Prilezhaeva in 1966-1986.

Research Areas and Key Results

Studying new domino reactions with a view to create a fundamental methodology of regio- and stereoselective synthesis of functionally substituted carbo- and heterocycles with practically useful properties.The following types of domino reactions have been studied: SN2 reaction -> Thorpe-Ziegler reaction -> Thorpe-Guareschi reaction; Knoevenagel reaction -> Michael reaction -> Thorpe –Ziegler hetero reaction; cross-combinations of domino reactions.

Developing regioselective methods for preparation of N-, O-, and S-containing organic compounds – drugs and drug candidates and their intermediates for treatment of cancer (prostate cancer, sarcoma, and with a DNA replication inhibiting function), blood thrombosis, and as cardiotonics.

Designing new regioselective environment-friendly methods for the synthesis of fluorinated  heterocycles. Study of the structure, reactivity and biological activity of fluorinated compounds in order to create a fundamental methodology for the synthesis of F-, O-, S-, and N-containing heterocycles.

Innovative activity. Ten-year collaboration of ZIOC RAS and Russian Cardiology Research and Production Complex resulted in finding original substances with pronounced antiarrhythmic properties with higher activity than the known drugs applied in the clinic. These have been covered by a RF patent No. 2379287 “Substituted sulfones and sulfoxides having antiarrhythmic activity and medications and pharmaceutical compositions on their basis” (Arzamastsev E.V., Laba V.I., Sviridova A.V., Mironova M.I., and Terekhova O.A.) with invention priority dated August 14, 2008 (registered in the State Register of Inventions of the Russian Federation on January 20, 2010 in cooperation with Russian Cardiological Research and Production Complex of the Federal Agency for High-Technology Medical Care (Rosmedtekhnologii).

Лаборатория 25

Recent publications:

  1. M. Shestopalov, A.A. Shestopalov. Ring containing Phosphorus. In: Comprehensive Heterocyclic Chemistri III. Editor A. R. Katritzky. Vol 14. Eight-membered and larger Heterocyclic rings and their fused derivatives other seven-membered rings. Volume Edit. G. R. Newkome, Elsevier, 2008, p. 901-944.
  2. Shestopalov, A. M.; Rodinovskaya, L. A.; Shestopalov, A. A.; Gromova, A. V.; Fedorov, A. E.; Gakh, A. A. Synthesis and reactions of fluorinated nicotinonitriles. In: Fluorinated Heterocycles; Gakh, A. A., Kirk, K. L., Eds.; ACS Symposium Series 1003; Oxford University Press/American Chemical Society: Washington, DC, 2009; pp 263-280.
  3. Anatoliy M. Shestopalov, Alexander A. Shestopalov, Lyudmila A. Rodinovskaya, Anna V. Gromova. Synthesis of Ring Fluorinated Pyridines. In: Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications; Viacheslav A. Petrov Ed., John Wiley & Sons, Inc., Hoboken, New Jersey, 2009, Part I, Chaper 6, pp 243-271.
  4. Y.M. Litvinov, A.M. Shestopalov. Synthesis, Structure, Chemical Reactivity and Practical Significance of 2-Amino-4H-pyrans. In book "Advances in Heterocyclic Chemistry", edited by Alan R. Katritzky. Vol. 103, Chapter 3, ELSEVIER, 2011, p. 175-260.
  5. A.M. Shestopalov, A.A. Shestopalov, L.A. Rodinovskaya. Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles. Synthesis. 2008, 1, 1-25.
  6. Victor E. Kalugin, Anatoly M. Shestopalov. A convenient synthesis of benzofuro[3,2-c]isoquinolines and naphtho[1',2':4,5]furo[3,2-c]isoquinolines. Tetrahedron Letters. 2011, 52, 1557–1560.
  7. A.M. Shestopalov, L.A. Rodinovskaya, A.A. Shestopalov. Synthesis of substituted thiazolo[4,5-b]pyridines and other annulated heterocycles via SN2 -> Thorpe-Ziegler -> Thorpe-Guareschi domino reactions. Tetrahedron, 2010, 66, N46, 8945-8948.
  8. Anatoliy M. Shestopalov, Lyudmila A. Rodinovskaya and Alexander A. Shestopalov. Combinatorial Synthesis of Substituted Thieno[3,2-b]pyridines and Other Annulated Heterocycles via New SN2 -> Thorpe-Ziegler -> Thorpe-Guareschi Domino Reactions. J. Comb. Chem., 2010, 12(1), 9–12.
  9. A.M. Shestopalov, A.A. Shestopalov, L.A. Rodinovskaya, A.V. Gromova. One-Step Synthesis of Substituted 3,5-Dicyanospiro-4-(-piperidine-4')-1H,4H–dihidropyridine-2-thiolates and 2,6-Diamino-3,5-dicyanospiro-[4(-piperidine-4') or (2-oxoindole-3')]-4H-thiopyranes. Phosphor, Sulfur, and Siliсon and Related Elements. 2009, 184, 1100-1114.
  10. A.M. Shestopalov, L.A. Rodinovskaya, A.E. Fedorov, V.E. Kalugin, K.G. Nikishin, A.A. Shestopalov, A.A. Gakh. Synthesis of 3-Cyano-2-fluoropyridines. Journal of Fluorine Chemistry, 2009, 130, 236-240.
  11. Yuri M. Litvinov, Alexander A. Shestopalov, Lyudmila A. Rodinovskaya, and Anatoliy M. Shestopalov. New convenient four-component synthesis of 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles and one-pot synthesis of 6'-aminospiro[(3H)-indol-3,4'-pyrano[2,3-c]pyrazol]-(1H)-2-on-5'-carbonitriles. J. Comb. Chem. 2009, 11, 914–919.
  12. Anatoliy M. Shestopalov, Alexander E. Fedorov, Liudmila A. Rodinovskaya, Alexander A. Shestopalov, Andrei A. Gakh. Microwave-assisted synthesis of substituted fluoroazines using KF.2H2O. Tetrahedron Letters, 2009, 50, 5257-5259.
  13. L.A. Rodinovskaya, A, M. Shestopalov, A. V. Gromova, A. A. Shestopalov. One-Pot Synthesis of Diverse 4-Di(tri)fluoromethyl-3-cyanopyridine-2(1H)-thiones and Their Utilities in the Cascade Synthesis of Annulated Heterocycles. J. Comb.Chem. 2008, 10, 313-322.
  14. Y.M. Litvinov, V.Yu. Mortikov, A.M. Shestopalov. Versatile Three-Component Procedure for Combinatorial Synthesis of 2-Aminospiro[(3'H)-indol-3',4-(4H)-pyrans]. J. Comb. Chem. 2008, 10(5), 741 – 745.
  15. A.V. Samet, A.M. Shestopalov, D.N. Lutov, L.A. Rodinovskaya, A.A. Shestopalov, V.V. Semenov. Preparation of chiral cyclopropanes with a carbohydrate fragment from levoglucosenone. Tetrahedron Asymmetry. 2007, N 18, p. 1986-1989.

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Congratulations! Valentine Ananikov has been elected to Academia Europaea! The European Academy of Sciences (Academia Europaea) was founded in 1988. It unites about four thousand globally acknowledged experts in mathematics, medicine, natural sciences, humanities, law, economy, and social and political sciences from many countries of Europe. Among its members are also European scientists who live in other regions of the world. Currently, it includes seventy two Nobel laureates and it should be highlighted that many of them were elected to the Academy before winning the Prize.
We are happy to invite you to Zelinsky Institute of Organic Chemistry to take part in the International Conference ChemTrends-2018 on Organic & Hybrid Functional Materials and Additive Technologies to be held on September 23-28, 2018.
Professor Mario Pargliaro Lecturing at Zelinsky Institute Prof Mario Pagliaro (Palermo Italy) gave two talks on June 8th and 9th.
Selective In-Situ Metal Azide Reactions Alexey Sukhorukov, N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia, and colleagues studied the selective reactions of in-situ generated metal azides on N,N-bis(oxy)enamines. By combining readily generated bis(oxy)enamine substrates with sodium azide and one of a variety of metal salts (including Mg, Cu, Zn, Co, and Ni), the researchers showed that the metal cation selectively alters the mechanism to favor the formation of specific organoazide products.
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