Department of Organic Chemistry, lab #4231

Chemistry of Strained Nitrogen-Containing Heterocycles in Functional Molecular Design

Short URL for media https://go.spbu.ru/rgkhlebnikov

Saint Petersburg State University, Institute of Chemistry
26 Universitetskii prospect, 198504 St. Petersburg, Russia
Tel. 007-812-4289344, This email address is being protected from spambots. You need JavaScript enabled to view it., Lab. 4231

Group members

Head of the group: Khlebnikov Alexander F. Doctor of chemical sciences, professor.

Group members

  • Konev Alexander S., PhD, Associate Professor;
  • Tomashenko Olesya A., PhD, Senior Researcher;
  • Galenko Ekaterina E., PhD, Assistant,
  • Students and PhD students

Collaborators

  • Prof. Balova I.A. (SPbU);
  • Prof. Tunik S.P. (SPbU);
  • Prof. K. Yamanouchi (University of Tokyo),
  • Prof. H. Heimgartner (University of Zurich),
  • Prof. G. Mlostoń (University of Łódź)
  • Prof. Tkachenko N.V. (Tampere University)

Research

I. Chemistry of nitrogen-containing heterocyclic compounds

• Synthesis and use of azirines and isoxazoles as molecular building blocks for the synthesis of new heterocyclic systems and ligands for metal complexes

Hlebnikov1

RG Khlebnikov 05RG Khlebnikov 06


• N-Ylides, carbenoids, nitrenoids and radical and other intermediates: generation and use in heterocyclic synthesis

Hlebnikov2RG Khlebnikov 08


• Multicatalysis in the synthesis of heterocycles

Khlebnikov 3RG Khlebnikov 10


II. Directional synthesis of compounds with useful properties on the basis of strained molecules

• Search for new approaches to the synthesis of nanoscale fullerene-containing systems

Hlebnikov4RG Khlebnikov 12

• Synthesis of heterocycles with useful photophysical properties, promising for use in sensors and photovoltaic devices and effective as ligands for metal complexes

Khlebnikov 5


III. Quantum-chemical calculations to understand the mechanisms of reactions, the reactivity of intermediates and the rational search for reaction partners

Hlebnikov6

Selected Publications

978 3 319 24960 5 A. F. Khlebnikov, M. S. Novikov. Ring Expansions of Azirines and Azetines. Topics in Heterocyclic Chemistry, DOI: 10.1007/7081_2015_154, (Chapter in Synthesis of 4- To 7-Membered Heterocycles by Ring Expansion: Aza-, Oxa- And Thiaheterocyclic Small-Ring Systems, M.D. Hooghe,H.-J. Ha Eds, 2016, Springer; ISBN: 9783319249582; ISBN-10: 3319249584)

Recent reviews

RG Khlebnikov 02 Khlebnikov A. F., Novikov M. S., Rostovskii N. V. Advances in 2H-azirine chemistry: A seven-year update. Tetrahedron 2019, 75, 2555-2624, DOI: 10.1016/j.tet.2019.03.040
RG Khlebnikov 03 Funt L. D., Novikov M. S., Khlebnikov A. F. New applications of pyridinium ylides toward heterocyclic synthesis. Tetrahedron 2020, 76, 131415; DOI: 10.1016/j.tet.2020.131415.

Synthesis and use of azirines and isoxazoles as molecular building blocks for the synthesis of new heterocyclic systems and ligands for metal complexes

  • Agafonova A. V., Funt L. D., Novikov M. S., Khlebnikov A. F. An isoxazole strategy for the synthesis of alkyl 5-amino-4-cyano-1H-pyrrole-2-carboxylates – versatile building blocks for assembling pyrrolo-fused heterocycles. Org. Biomol. Chem. 2021, 19, DOI: 10.1039/d1ob00053e.
  • Galenko, E. E.; Bodunov, V. A.; Kryukova, M. A.; Novikov, M. S.; Khlebnikov, A. F. Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds. J. Org. Chem. 2021, 86, DOI: 10.1021/acs.joc.0c02928.
  • Galenko E. E., Yu. V. Kryukova M. A,. Novikov M. S, Khlebnikov A. F. Synthesis of Bi‑, Ter‑, and Quaterpyridinecarboxylates via Propargylisoxazole−Pyridine Rearrangement. J. Org. Chem. 2020, 85, 6109-6122, DOI: 10.1021/acs.joc.0c00611;
  • Galenko E. E., Shakirova F. M., Bodunov V. A., Novikov M. S., Khlebnikov A. F. 1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles. Org. Biomol. Chem. 2020, 18, 2283–2296, DOI: 10.1039/D0OB00206B;
  • Funt L. D., Krivolapova Yu. V., Khoroshilova O. V., Novikov M. S., Khlebnikov A. F. 2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks. J. Org. Chem. 2020, 85, 4182-4194, DOI: 10.1021/acs.joc.9b03367;
  • Galenko E. E., Linnik S. A., Khoroshilova O. V., Novikov M. S., Khlebnikov A. F. Isoxazole Strategy for the Synthesis of α-Aminopyrrole Derivatives. J. Org. Chem. 2019, 84, 11275-11285, DOI: 10.1021/acs.joc.9b01634;
  • Bodunov V. A., Galenko E. E., Sakharov P.A., Novikov M. S., Khlebnikov A. F. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1H-pyrroles: Synthesis of Benzo/Furo/Thieno[e]-Fused 1H-Indol-7-oles and Their Transformations. J. Org. Chem. 2019, 84, 10388-10401, DOI: 10.1021/acs.joc.9b01573;
  • Galenko E. E., Novikov M. S., Shakirova F. M., Shakirova J. R., Kornyakov I. V., Bodunov V. A., Khlebnikov A. F. An Isoxazole Strategy for the Synthesis of 2,2’-Bipyridine Ligands: Symmetrical and Unsymmetrical 6,6’-Binicotinates, 2,2’-Bipyridine-5-carboxylates, and Their Metal Complexes. J. Org. Chem. 2019, 84, 3524-3536, DOI: 10.1021/acs.joc.9b00115;
  • Mikhailov K. I., Galenko E. E., Galenko A. V., Novikov M. S., Ivanov A. Yu., Starova G. L., Khlebnikov A. F. Fe(II)-Catalyzed isomerization of 5-chloroisoxazoles to 2H-azirine-2-carbonylchlorides as a key stage in the synthesis of pyrazole-nitrogen heterocycle dyads. J. Org. Chem. 2018, 83, 3177–3187; DOI: 10.1021/acs.joc.8b00069;
  • Funt L. D., Tomashenko O. A., Novikov M. S., Khlebnikov A. F. An azirine strategy for the synthesis of alkyl 4-amino-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates. Synthesis 2018, 50, 4809-4822; DOI: 10.1055/s-0037-1610840;
  • Bodunov V. A., Galenko E. E., Galenko A. V., Novikov M. S., Khlebnikov A. F. Synthesis of Substituted Indole-3-carboxylates by Fe(II)-Catalyzed Domino Isomerization of 3-Alkyl/aryl-4-aryl-5-methoxyisoxazoles. Synthesis 2018, 50, 2784-2798, DOI: 10.1055/s-0036-1591576;
  • Galenko E. E., Ivanov V. K., Novikov M. S., Khlebnikov A. F. Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles. Tetrahedron 2018, 74, 6288-6298; DOI: 10.1016/j.tet.2018.09.015;
  • Sakharov P. A., Novikov M. S., Khlebnikov A. F. 2-Diazoacetyl-2H-azirines: Source of a Variety of 2H-Azirine Building Blocks with Orthogonal and Domino Reactivity. J. Org. Chem. 2018, 83, 8304-8314; DOI: 10.1021/acs.joc.8b01004;
  • Galenko E. E., Bodunov V. A., Galenko A. V., Novikov M. S., Khlebnikov A. F. Fe(II)-Catalyzed Isomerization of 4-Vinylisoxazoles into Pyrroles. J. Org. Chem. 2017, 82, 8568−8579. DOI: 10.1021/acs.joc.7b01351;
  • Galenko E. E., Khlebnikov, A. F.; Novikov, M. S. Isoxazole-azirine isomerization as a reactivity switch in the synthesis of heterocycles. Chem. Heterocycl. Compd. 2016, 52, 637–650. DOI: 10.1007/s10593-016-1944-1;
  • Galenko E. E., Galenko A. V., Khlebnikov A. F., Novikov M. S., Shakirova J. R. Synthesis and intramolecular azo coupling of 4-diazopyrrole-2-carboxylates: selective approach to benzo and hetero [c]-fused 6H-pyrrolo[3,4-c]pyridazine-5-carboxylates. J. Org. Chem. 2016, 81, 8495−8507; DOI: 10.1021/acs.joc.6b01662;
  • Galenko A. V., Khlebnikov A. F., Novikov M. S., Pakalnis V. V., Rostovskii N. V. Recent advances in isoxazole chemistry. Russ. Chem. Rev. 2015, 84, 335–377. DOI:10.1070/RCR4503;
  • Galenko A. V., Khlebnikov A. F., Novikov M. S., Avdontseva M. S. Synthesis of 3-(1,2-dioxoethyl)- and 2,3-dicarbonyl-containing pyrroles. Tetrahedron 2015, 71, 1940–1951. DOI: 10.1016/j.tet.2015.02.030;
  • Khlebnikov, A. F.; Novikov, M. S.; Pakalnis, V. V.; Iakovenko, R. O.; Yufit D. S. Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems. Belst. J. Org. Chem. 2014, 10, 784-793. DOI:10.3762/bjoc.10.74;
  • Khlebnikov, A. F.; Novikov, M. S. Recent advances in 2H-azirine chemistry. Tetrahedron 2013, 69, 3363-3401. DOI:10.1016/j.tet.2013.02.020,

Ylides, carbenoids, nitrenoids and other intermediates: generation and use in heterocyclic synthesis

  • Galenko, E. E.; Bodunov, V. A.; Kryukova, M. A.; Novikov, M. S.; Khlebnikov, A. F. Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds. J. Org. Chem. 2021, 86, DOI: 10.1021/acs.joc.0c02928.
  • Funt L. D., Krivolapova Yu. V., Khoroshilova O. V., Novikov M. S., Khlebnikov A. F. 2H-Azirine-2-carbonyl Azides: Preparation and Use as N-Heterocyclic Building Blocks. J. Org. Chem. 2020, 85, 4182-4194, DOI: 10.1021/acs.joc.9b03367;
  • Galenko E. E., Shakirova F. M., Bodunov V. A., Novikov M. S., Khlebnikov A. F. 1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles. Org. Biomol. Chem. 2020, 18, 2283–2296, DOI: 10.1039/D0OB00206B;
  • Galenko E. E., Linnik S. A., Khoroshilova O. V., Novikov M. S., Khlebnikov A. F. Isoxazole Strategy for the Synthesis of α-Aminopyrrole Derivatives. J. Org. Chem. 2019, 84, 11275-11285, DOI: 10.1021/acs.joc.9b01634;
  • Bodunov V. A., Galenko E. E., Sakharov P.A., Novikov M. S., Khlebnikov A. F. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1H-pyrroles: Synthesis of Benzo/Furo/Thieno[e]-Fused 1H-Indol-7-oles and Their Transformations. J. Org. Chem. 2019, 84, 10388-10401, DOI: 10.1021/acs.joc.9b01573;
  • Funt L. D., Novikov M. S., Starova G. L., Khlebnikov A. F. Synthesis and properties of new heterocyclic betaines: 4-Aryl-5-(methoxycarbonyl)-2-oxo-3-(pyridin-1-ium-1-yl)-2,3-dihydro-1H-pyrrol-3-ides. Tetrahedron 2018, 74, 2466-2474, DOI: 10.1016/j.tet.2018.03.071;
  • Kornilova T. A., Kostikov R. R., Khlebnikov A. F., Zenkevich I. G. Comparative characterization of thermal isomerization rates of 6‐phenyl‐1,5‐diazabicyclo[3.1.0]hexane at convection and microwave heating. J. Phys. Org. Chem. 2018, 31 (7), e3843; DOI: 10.1002/poc.3843;
  • Funt L.D., Tomashenko O.A., Mosiagin I.P., Novikov M.S., Khlebnikov A.F. Synthesis of Pyrrolotriazoloisoquinoline Frameworks by Intramolecular Cu-Mediated or Free Radical Arylation of Triazoles. J. Org. Chem. 2017, 82, 7583-7594. DOI:10.1021/acs.joc.7b01341;
  • Gaisina K. R., Khlebnikov A. F., Novikov M. S. Non-pericyclic cycloaddition of gem-difluorosubstituted azomethine ylides to the C=O bond: computational study and synthesis of fluorinated oxazole derivatives. Org. Biomol. Chem. 2017, 15, 4579-4586. DOI: 10.1039/C7OB00521K;
  • Tomashenko O. A., Novikov M. S., Khlebnikov A. F. NHC as the Guiding Factor in a Copper-Catalyzed Intramolecular C Arylation of Pyrrolylimidazolium Salts: Synthesis of Luminescent Heterotetracyclic Frameworks. J. Org. Chem. 2017, 82, 616-623. DOI: 10.1021/acs.joc. 6b02627;
  • Funt L. D., Tomashenko O. A., Khlebnikov A. F., Novikov M. S., Ivanov Yu. A. Synthesis, Transformations of Pyrrole- and 1,2,4-Triazole-Containing Ensembles, and Generation of Pyrrole-Substituted Triazole NHC. J. Org. Chem. 2016, 81, 11210-11221. DOI: 10.1021/acs.joc.6b02200;
  • Khlebnikov A. F., Novikov M. S., Gorbunova Y. G., Galenko E. E., Mikhailov K. I., Pakalnis V. V., Avdontceva M. S. Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines. Belst. J. Org. Chem. 2014, 10, 1896-1905. DOI:10.3762/bjoc.10.197;
  • Khlebnikov A. F., Tomashenko O. A., Funt L. D., Novikov M. S. Simple Approach to Pyrrolylimidazole Derivatives by Azirine Ring Expansion with Imidazolium Ylides. Org. Biomol. Chem. 2014, 12, 6598-6609. DOI: 10.1039/c4ob00865k;
  • Khlebnikov A. F., Konev A. S., Virtsev A. A., Yufit D. S., Mlostoń G., Heimgartner H. Concerted vs. Non-Concerted 1,3-Dipolar Cycloadditions of Azomethine Ylides to Electron-Deficient Dialkyl 2,3-Dicyanobut-2-enedioates. Helv. Chim. Acta. 2014, 97, 453-470. DOI:10.1002/hlca.201300405,

Multicatalysis in the synthesis of heterocycles

  • Galenko E. E., Yu. V. Kryukova M. A,. Novikov M. S, Khlebnikov A. F. Synthesis of Bi‑, Ter‑, and Quaterpyridinecarboxylates via Propargylisoxazole−Pyridine Rearrangement. J. Org. Chem. 2020, 85, 6109-6122, DOI: 10.1021/acs.joc.0c00611;
  • Bodunov V. A., Galenko E. E., Sakharov P.A., Novikov M. S., Khlebnikov A. F. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1H-pyrroles: Synthesis of Benzo/Furo/Thieno[e]-Fused 1H-Indol-7-oles and Their Transformations. J. Org. Chem. 2019, 84, 10388-10401, DOI: 10.1021/acs.joc.9b01573;
  • Galenko E. E., Novikov M. S., Shakirova F. M., Shakirova J. R., Kornyakov I. V., Bodunov V. A., Khlebnikov A. F. An Isoxazole Strategy for the Synthesis of 2,2’-Bipyridine Ligands: Symmetrical and Unsymmetrical 6,6’-Binicotinates, 2,2’-Bipyridine-5-carboxylates, and Their Metal Complexes. J. Org. Chem. 2019, 84, 3524-3536, DOI: 10.1021/acs.joc.9b00115;
  • Funt L. D., Tomashenko O. A., Novikov M. S., Khlebnikov A. F. An azirine strategy for the synthesis of alkyl 4-amino-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates. Synthesis 2018, 50, 4809-4822, DOI: 10.1055/s-0037-1610840;
  • Galenko E. E., Ivanov V. K., Novikov M. S., Khlebnikov A. F. Synthesis of N-aminopyrazoles by Fe(II)-catalyzed rearrangement of 4-hydrazonomethyl-substituted isoxazoles. Tetrahedron 2018, 74, 6288-6298, DOI: 10.1016/j.tet.2018.09.015;
  • Galenko A. V., Galenko E. E., Shakirova F. M., Novikov M. S., Khlebnikov A. F. Fe(II)/Au(I) Relay Catalyzed Propargylisoxazole to Pyridine Isomerization: Access to 6-Halonicotinates. J. Org. Chem. 2017, 82, 5367-5379. DOI: 10.1021/acs.joc.7b00736;
  • Galenko E. E., Tomashenko O. A., Khlebnikov A. F., Novikov M. S. Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives. Beilstein J. Org. Chem. 2015, 11, 1732–1740. DOI:10.3762/bjoc.11.189;
  • Galenko E. E., Tomashenko O. A., Khlebnikov A. F., Novikov M. S. Metal/organo relay catalysis in a one‐pot synthesis of methyl 4-aminopyrrole‐2‐carboxylates from 5‐methoxyisoxazoles and pyridinium ylides. Org. Biomol. Chem. 2015, 13, 9825-9833; DOI: 10.1039/c5ob01537e;
  • Galenko E. E., Galenko A. V., Khlebnikov A. F., Novikov M. S. Domino transformation of isoxazoles to 2,4-dicarbonylpyrroles under Fe/Ni relay catalysis. RSC Advances 2015, 5, 18172-18176. DOI: 10.1039/C5RA01889G.

Synthesis and use of aziridines as effective sources of active intermediates for the construction of complex molecular systems

  • Kazakova A. V., Androsov D. V., Konev A. S., Khlebnikov A. F. Magnesium acetate – an effective electrophilic activator of the carbonyl group in transesterification of dialkylaziridine dicarboxylates. Chem. Heterocycl. Compd. 2020, 56, 875–880, DOI: 10.1007/s10593-020-02744-y.
  • Kazakova A. V., Konev A. S., Zorin I. M., Poshekhonov V. A., Korzhikov-Vlakh V. A., Khlebnikov A. F. PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines. Org. Biomol. Chem. 2019, 17, 9864–9873, DOI: 10.1039/c9ob01949a;
  • Lukyanov D.A., Funt L.D., Konev A.S., Povolotskiy A. V., Vereshchagin A. A., Levin O.V., Khlebnikov A.F. Novel homogeneous photocatalyst for oxygen to hydrogen peroxide reduction in aqueous media. Photochem. Photobiol. Sci. 2019, 18, 1982-1989, DOI: 10.1039/C9PP00206E;
  • Androsov D. V., Strelnikov A. A., Konev A. S., Lukyanov D. A., Kazakova A. V., Levin O. V., Khlebnikov A. F. Photogalvanic effect in porphyrin-pyrrolo[3´,4´:1,9]-(C60-Ih)[5,6]fullerene-2´,5´-dicarboxylate systems. Russ. Chem. Bull. 2019, 68, 825-831, DOI: 10.1007/s11172-019-2491-6;
  • Lukyanov D. A., Konev A. S., Amsharov K. Yu., Khlebnikov A. F., Hirsch A. Diastereospecific and highly site-selective functionalization of C70 fullerene by reaction with diethyl N-arylaziridine-2,3-dicarboxylates. J. Org. Chem. 2018, 83, 14146-14151, DOI: 10.1021/acs.joc.8b02240;
  • Strelnikov A. A., Androsov D. V., Konev A. S., Lukyanov D. A., Khlebnikov A. F., Povolotskiy A. V., Yamanouchi K. Triaryl-substituted pyrrolo-p-phenylene-linked porphyrin-fullerene dyads: Expanding the structural diversity of photoactive materials. Tetrahedron 2018, 74, 3007-3019, DOI: 10.1016/j.tet.2018.04.084;
  • Lukyanov, D. A.; Konev, A. S.; Amsharov, K. Yu.; Khlebnikov, A. F.; Hirsch A. Diastereospecific and highly site-selective functionalization of C70 fullerene by reaction with diethyl N-arylaziridine-2,3-dicarboxylates. J. Org. Chem., 2018, 83, 14146-14151; DOI: 10.1021/acs.joc.8b02240;
  • Strelnikov A. A., Androsov D. V., Konev A. S., Lukyanov D. A., Khlebnikov A. F., Povolotskiy A. V., Yamanouchi K. Triaryl-substituted pyrrolo-p-phenylene-linked porphyrin-fullerene dyads: Expanding the structural diversity of photoactive materials. Tetrahedron 2018, 74, 3007-3019, DOI: 10.1016/j.tet.2018.04.084;
  • Konev A. S., Khlebnikov A. F., Levin O. V., Lukyanov D. A., Zorin I. M. Photocurrent in Multilayered Assemblies of Porphyrin–Fullerene Covalent Dyads: Evidence for Channels for Charge Transport. ChemSusChem. 2016, 9, 676–686. DOI:10.1002/cssc.201501686;
  • Konev A. S., Khlebnikov A. F., Prolubnikov P. I., Mereshchenko A. S., Povolotskiy A. V., Levin O. V., Hirsch A. Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge-Separated States on a Microsecond Lifetime Scale. Chem. Eur. J. 2015, 21, 1237–1250. DOI:10.1002/chem.201404435;
  • Konev A. S., Lukyanov D. A., Vlasov P. S., Levin O. V., Virtsev A. A., Kislyakov I. M.; Khlebnikov A. F. The Implication of 1,3-Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main-Chain Porphyrin Oligomers. Macromol. Chem. Phys. 2014, 215, 516-529. DOI: 10.1002/macp.201300679;
  • Konev A. S., Khlebnikov A. F., Nikiforova T. G., Virtsev A. A., Frauendorf H. Synthesis and spectroscopic and electrochemical properties of an axially symmetric fullerene-porphyrin dyad with a rigid pyrrolo[3,4-c]pyrrole spacer. J. Org. Chem. 2013, 78, 2542-2552. DOI: 10.1021/jo302763a;

Directional synthesis of compounds with useful properties on the basis of strained molecules

  • Kazakova A. V., Rubicheva L. G., Konev A. S., Khlebnikov A. F. Stereoselective synthesis of PEGylated azoles via 1,3-dipolar cycloaddition. Tetrahedron 2021, 77, 131774, DOI: 10.1016/j.tet.2020.131774.
  • Kozina D. O., Shakirova J. R., Galenko E. E., Porsev V. V., Gurzhiy V. V., Khlebnikov A. F., Tunik S. P. Unusual Reactivity and Photophysical Properties of Platinum(II) Pincer Complexes Containing 6,6'‐Diphenyl‐2,2'‐bipyridine Ligands. Europ. J. Inorg. Chem. 2021, 117-125, DOI: 10.1002/ejic.202000827.
  • Strelnikov A. A., Konev A. S., Levin O. V., Khlebnikov A. F., Iwasaki, A.; Yamanouchi, K.; Tkachenko, N. V. Switching competition between electron and energy transfers in porphyrin-fullerene dyads. J. Phys. Chem. B 2020, 124, 10899–10912, DOI: 10.1021/acs.jpcb.0c06931.
  • Plass F., Lukyanov D. A., Konev A. S., Kahnt A., Amsharov K. Y., Khlebnikov A. F., Guldi D. M. Controlling the Charge Transfer Mechanism and Efficiency by Means of Different C70 Regioisomeric Adducts. Small Structures 2020, 1, 2000012, DOI: 10.1002/sstr.202000012.
  • Galenko E. E., Yu. V. Kryukova M. A,. Novikov M. S, Khlebnikov A. F. Synthesis of Bi‑, Ter‑, and Quaterpyridinecarboxylates via Propargylisoxazole−Pyridine Rearrangement. J. Org. Chem. 2020, 85, 6109-6122, DOI: 10.1021/acs.joc.0c00611;
  • Shakirova J. R., Shevchenko N. N., Baigildin V. A., Chelushkin. P. S., Khlebnikov A. F., Tomashenko O. A., Solomatina A. I., Starova G. L., Tunik S. P. Eu-Based Phosphorescence Lifetime Polymer Nanothermometer: A Nanoemulsion Polymerization Approach to Eliminate Quenching of Eu Emission in Aqueous Media. ACS Appl. Polym. Mater. 2020, 2, 537-547, DOI: 10.1021/acsapm.9b00952;
  • Kazakova A. V., Konev A. S., Zorin I. M., Poshekhonov V. A., Korzhikov-Vlakh V. A., Khlebnikov A. F. PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines. Org. Biomol. Chem. 2019, 17, 9864–9873, DOI: 10.1039/c9ob01949a;
  • Lukyanov D.A., Funt L.D., Konev A.S., Povolotskiy A. V., Vereshchagin A. A., Levin O.V., Khlebnikov A.F. Novel homogeneous photocatalyst for oxygen to hydrogen peroxide reduction in aqueous media. Photochem. Photobiol. Sci. 2019, 18, 1982-1989, DOI: 10.1039/C9PP00206E;
  • Bodunov V. A., Galenko E. E., Sakharov P.A., Novikov M. S., Khlebnikov A. F. Selective Cu-Catalyzed Intramolecular Annulation of 3-Aryl/Heteryl-2-(diazoacetyl)-1H-pyrroles: Synthesis of Benzo/Furo/Thieno[e]-Fused 1H-Indol-7-oles and Their Transformations. J. Org. Chem. 2019, 84, 10388-10401, DOI: 10.1021/acs.joc.9b01573;
  • Galenko E. E., Novikov M. S., Shakirova F. M., Shakirova J. R., Kornyakov I. V., Bodunov V. A., Khlebnikov A. F. An Isoxazole Strategy for the Synthesis of 2,2’-Bipyridine Ligands: Symmetrical and Unsymmetrical 6,6’-Binicotinates, 2,2’-Bipyridine-5-carboxylates, and Their Metal Complexes. J. Org. Chem. 2019, 84, 3524-3536, DOI: 10.1021/acs.joc.9b00115;
  • Shakirova J. R., Tomashenko O. A., Galenko E. E., Khlebnikov A. F., Hirva P., Starova G. L., Su S. H., Chou P. T., Tunik S. P.. Metalated Ir(III) Complexes Based on the Luminescent Diimine Ligands: Synthesis and Photophysical Study. Inorg. Chem. 2018, 57, 6853-6864, DOI: 10.1021/acs.inorgchem.8b00390;
  • Galenko E. E.; Galenko A. V.; Novikov M. S.; Khlebnikov A. F.; Kudryavtsev I. V.; Terpilowski M. A.; Serebriakova M. K.; Trulioff A. S.; Goncharov N. V. 4-Diazo and 4-(Triaz-1-en-1-yl)-1H-pyrrole-2-carboxylates as Agents Inducing Apoptosis. ChemistrySelect 2017, 2, 7508-7513. doi: 10.1002/slct.201701538;
  • Shakirova J. R., Tomashenko O. A., Grachova E. V., Starova G. L., Sizov V. V., Khlebnikov A. F., Tunik S. P. Gold(I)-alkynyl complexes with a new type N-donor heterocyclic ligand: Synthesis and photophysical properties. Eur. J. Inorg. Chem., 2017, 4180-4186DOI: 10.1002/ejic.201700731;
  • Koshel E. I., Tomashenko O. A., Khlebnikov A. F., Gaginskaya E. R., Saifitdinova A. F., Tunik S. P. A new nuclear heterocyclic fluorescent dye – a promising tool for karyology and cytogenetics. Chromosome Res. 2016, 24 (Suppl 1), S29–S30. DOI 10.1007/s10577-016-9532-x;
  • Konev A. S., Khlebnikov A. F., Levin O. V., Lukyanov D. A., Zorin I. M. Photocurrent in Multilayered Assemblies of Porphyrin–Fullerene Covalent Dyads: Evidence for Channels for Charge Transport. ChemSusChem. 2016, 9, 676–686. DOI:10.1002/cssc.201501686;
  • Tomashenko O. A., Khlebnikov A. F., Mosiagin I. P., Novikov M. S., Grachova E. V., Shakirova J. R., Tunik S. P. A new heterocyclic skeleton with highly tunable absorbtion/emission wavelength via H-bonding RSC Adv. 2015, 5, 94551-94561; DOI: 10.1039/C5RA17755C.