Valery N. Kalinin

 

Prof., D. Sc.

 

Head of the Laboratory for Fine Organic Synthesis

Phone: 7-499-135-93-14

Fax:  7-499-135-65-49

E-mail: vkalin@ineos.ac.ru

 

 

Scope of Interests:

Chemistry of Carboranes

Chemistry of Alkaloids

Medicinal Chemistry

Meso-ionic Compounds

Transition Metal Complex Catalysis

Cross-coupling reactions

Heterocyclization reactions

Scientific Achievements:

• One of the founders of the carborane chemistry (Russian State Prise Winner, 1996).
• Pioneering studies on applications of the organometallic chemistry approaches and transition metal complex catalysis to syntheses of the compounds with a tentative pharmacological activity. Specifically, the items have been elaborated as follows:

- new ternary Pd-catalyzed cyclizations of o-iodophenols or o-iodoanilines with acetylenes and carbon monoxide producing flavones, chromones or quinolones;

- methods for preparations of a variety of carborane derivatives for use in photodynamic (PDT) or boron neutron capture (BNCT)  therapies of cancer;

- the functionalizations of meso-ionic compounds (sydnones, sydnone imines, munchnone imines) via their metalated derivatives;

- new approaches to preparations of 6,7-benzomorphanes or C-norbenzomorphanes with the use of benzyl functionalizations of aromatic compounds via their tricarbonyl chromium complexes;

- new methods for modifying the morphinane alkaloid derivatives (N-arylation, Pd-catalyzed transformations of allylic moieties of the molecules);

- methods for preparations of both the fluorinated and non-fluorinated cyclobutene, polycyclic or heterocyclic compounds using [2+2]- or  [4+2]-cycloaddition reactions with participation of azadienes or highly reactive acetylenes activated by trifluoroacetyl or other electron withdrawing groups.

 

 

Selected Publications:

1. S.Torri, H.Okumoto, L.Xu, M.Sadakane, M.V.Shostakovsky, A.B.Ponomaryov, V.N.Kalinin. Syntheses of chromones and quinolones via Pd-catalyzed carbonylation of o-iodophenols and anilines in the presence of acetylenes. // Tetrahedron, 49, 6773-6784 (1993).
2. V.N.Kalinin, E.G.Rys, A.A.Tyutyunov, Z.A.Starikova, A.A.Korlyukov, V.A.Ol`shevskaya, D.D.Sung, A.B.Ponomaryov, P.V.Petrovskii, E.Hey-Hawkins. The first carborane triflates: synthesis and reactivity of 1-trifluoromethanesulfonylmethyl- and 1,2-bis(trifluoromethanesulfonylmethyl)-o-carborane. // Dalton Trans., 903-908 (2005).
3. V.A.Ol’shevskaya, R.Ayuob, Zh.G.Brechko, P.V.Petrovskii, E.G.Kononova, G.L.Levit, V.P.Krasnov, V.N.Charushin, O.N.Chupakhin, V.N.Kalinin. Synthesis of Carborane Analogues of  -Aminobutanoic Acid. // J. Organometal. Chem., 690, 2761- 2765 (2005).
4. V.A.Ol’shevskaya, A.V.Zaitsev, V.N.Luzgina, T.T.Kondratieva, E.G.Kononova, P.V.Petrovskii, A.F.Mironov, V.N.Kalinin, A.A.Shtil. Novel boronated derivatives of 5,10,15,20-tetraphenylporphyrin: Synthesis and toxicity for drug-resistant tumor cells. // Bioorg. Med. Chem., 14, 109-120 (2006).
5. V.N.Kalinin, I.V.Shishkov, S.K.Moiseev, E.E.Shults, G.A.Tolstikov, N.I.Sosnina, P.V.Petrovskii, K.A.Lyssenko, H.Schmidhammer. Palladium-Catalyzed 2-Phenylethenylation of Codeine: 8-[(1E)-2-Phenylethenyl]codeinone Dimethyl Ketal as the Unexpected «Masked» Diene for the Preparation of 19-Substituted Diels-Alder Adducts of Thebaine. // Helv. Chim. Acta, 89, (5), 861-869 (2006).
6. S.N.Lebedev, I.A.Cherepanov, V.N. Kalinin. Lithium and copper derivatives of munchnone imines. // Mendeleev Commun., 215-216 (2003).
7. V.N.Kalinin, I.A.Cherepanov, S.K.Moiseev. Benzylic functionalization of (h⁶-alkylarene) chromiumtricarbonyl complexes. // J. Organometal. Chem., 536-537, 437-455 (1997).
8. S.K.Moiseev, I.V.Bakhanova, H.Schmidhammer, V.N.Kalinin. Synthesis of N-phenyl-substituted derivatives of morphine alkaloids. // Russ. Chem. Bull., 48, (3), 589-592 (1999), (Engl. Transl.).
9. A.B.Koldobskii, E.V.Solodova, I.A.Godovikov, V.N.Kalinin. Synthesis and unusual [2+2]-cycloaddition reactions of ethyl 4-chloro-2-oxobut-3-ynoate with unactivated alkenes. // Tetrahedron, 64, (40), 9555-9560 (2008).
10. A.B.Koldobskii, N.P.Tsvetkov, E.V.Solodova, V.N.Kalinin. 1-Bromo-2-trifluoroacetylcyclobutenes as the novel building blocks for the construction of trifluoromethyl substituted heterocycles. Part 1: The synthesis of 5-(trifluoromethyl)-2(5H)-furanones condensed with substituted cyclobutanes. // J. Fluor. Chem., 131, (6), 714-718 (2010).
11. S.N.Lebedev, I.A.Cherepanov, V.N. Kalinin. Lithium and copper derivatives of munchnone imines. // Mendeleev Commun., 215-216 (2003).
12. I.A.Cherepanov, N.V.Egorova, K.B.Martinovich, V.N. Kalinin. Organometallic derivatives of sydnone imines. // Dokl. Akad. Nauk (Russ.), 374, (1), 64-67 (2000).
13. V.P.Krasnov, G.L.Levit, V.N.Charushin, A.N.Grishakov, M.I.Kodess, V.N.Kalinin, V.A.Ol’shevskaya, O.N.Chupakhin. Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane. // Tetrahedron: Asymmetry, 13, 1833-1835 (2002).
14. S.C.Shim, J.G.Shim, D.Y.Lee, Y.Z.Youn, V.N.Kalinin. A new type of stabilized carbonucleophiles with a carboranyl group. // Bull. Korean Chem. Soc., 15, (11), 919-922 (1994).
15. I.A.Cherepanov, S.N.Lebedev, V.N.Kalinin. Functionalized sydnones through a facile metallation of 3-methyl-4-phenylsydnone. // Synlett, 667 (1998).
16. V.A.Ol’shevskaya, R.Ayuob, Z.G.Brechko, P.V.Petrovskii, E.G.Kononova, G.L.Levit, V.P.Krasnov, V.N.Charushin, O.N.Chupakhin, V.N.Kalinin. Synthesis of carborane analogues of g-aminobutanoic acid. // J. Organometal. Chem., 690, (11), 2761-2765 (2005).
17. S.E.Lyubimov, A.A.Tyutyunov, V.N.Kalinin, E.E.Said-Galiev, A.R.Khokhlov, P.V.Petrovskii, V.A.Davankov. Carboranylphosphites - new effective ligands for rhodium-catalyzed asymmetric hydrogenation of dimethyl itaconate. // Tetrahedron Lett., 48, (46), 8217-8219 (2007).