Organic Chemistry

RU

Publications in 2022

  1. Merkulova, E.A.; Kolobov, A.V.; Kuznetsov, M.A.; Spiridonova, D.V.; Pankova, A.S. Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides. Tetrahedron Lett. 2022, 94, 153715. doi: 10.1016/j.tetlet.2022.153715.
  2. Androsov, D.V.; Konev, A.S.; Khlebnikov, A.F. Aziridine strategy for stereospecific synthesis of 1′-alkyl/aryl-5′-aryl-2′,5′-dihydropyrrolofullerene-2′-carboxylates and NMR study of hindered 5′-aryl group rotation. Tetrahedron 2022, 111, 132734. doi: 10.1016/j.tet.2022.132734.
  3. Filatov, A.S.; Selivanov, S.I.; Shmakov, S.V.; Larina, A.G.; Boitsov, V.M.; Stepakov, A.V. An Experimental and Theoretical Study of the 1,3-Dipolar Cyclo addition of Alloxan-Derived Azomethine Ylides to Cyclopropenes. Synthesis. 2022, 54, 1803–1816, doi: 10.1055/a-1700-3115.
  4. Filatov, A.S.; Larina, A.G.; Petrov, M.L.; Boitsov, V.M.; Stepakov, A.V. Synthesis of Quinolino[1,2-c]quinazolin-6-one Derivatives via Formal (4+2)-Cycloaddition of Alkenes to Quinazolin-Derived N-Acyliminium Cations: An Experimental and Theoretical Study. Synthesis. 2022, 54, 2395–2414, doi: 10.1055/a-1755-2061.
  5. Zenkevich, I.G.; Arutyunov, Y.I.; Kopytin, K.A.; Mikhailov, I.Y.; Onuchak, L.A. Characteristics of the Anomalous Temperature Dependence of Gas Chromatographic Retention Indices of Polar Compounds on Packed Columns with a Nonpolar Phase. Russ. J. Phys. Chem. A 2022, 96, 654–663, doi: 10.1134/S003602442203030X.
  6. Efremova, M.M.; Rostovskii, N.V. The VIth International Symposium “The Chemistry of Diazo Compounds and Related Systems” (DIAZO 2021). Russ. J. Org. Chem. 2022, 58, 335–351, doi: 10.1134/S1070428022030113.
  7. Popova, E.A.; Pronina, Y.A.; Davtian, A.V.; Nepochatyi, G.D.; Petrov, M.L.; Boitsov, V.M.; Stepakov, A.V. Squaramide-Based Catalysts in Organic Synthesis (A Review). Russ. J. Gen. Chem. 2022, 92, 287–347, doi: 10.1134/S107036322203001X.
  8. Molchanov, A.P.; Efremova, M.M.; Kuznetsov, M.A. Cyclopropenes and methylenecyclopropanes in 1,3-dipolar cycloaddition reactions. Russ. Chem. Bull. 2022, 71, 620–650, doi: 10.1007/s11172-022-3460-z.
  9. Karpitskiy, D.A.; Bessonova, E.A.; Kartsova, L.A.; Tikhomirova, L.I. Development of approach for flavonoid profiling of biotechnological raw materials Iris sibirica L. by HPLC with high-resolution tandem mass spectrometry. Phytochem. Anal. 2022, 33, 869–878, doi: 10.1002/pca.3135.
  10. Stepakov, A.V.; Filatov, A.S.; Boitsov, V.M.; Lozovskiy, S.V. Diastereoselective cycloaddition of tosylpropadiene to azomethine ylides, derived from proline and carbonyl compounds: an experimental and DFT study. Phosphorus, Sulfur Silicon Relat. Elem. 2022, 197, 67–71, doi: 10.1080/10426507.2021.2017436.
  11. Shcherbakov, N.V.; Titov, G.D.; Chikunova, E.I.; Filippov, I.P.; Rostovskii, N.V.; Kukushkin, V.Y.; Dubovtsev, A.Y. Modular approach to non-aromatic and aromatic pyrroles through gold-catalyzed [3 + 2] cycloaddition of 2H-azirines and ynamides. Org. Chem. Front. 2022, 9, 5133–5140, doi: 10.1039/d2qo01105k.
  12. Agafonova, A.V.; Sakharov, P.A.; Smetanin, I.A.; Rostovskii, N.V.; Khlebnikov, A.F.; Novikov, M.S. Stannyl radical-mediated synthesis of 6H-1,3-oxazin-6-ones from 2-acyloxyazirines or whether free radicals can open the azirine ring? Org. Chem. Front. 2022, 9, 4118–4127, doi: 10.1039/d2qo00783e.
  13. Krivolapova, Y.V.; Tomashenko, O.A.; Funt, L.D.; Spiridonova, D.V.; Novikov, M.S.; Khlebnikov, A.F. Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines. Org. Biomol. Chem. 2022, 20, 5434–5443, doi: 10.1039/d2ob00908k.
  14. Kochurin, M.A.; Ismagilova, A.R.; Zakusilo, D.N.; Khoroshilova, O.V.; Boyarskaya, I.A.; Vasilyev, A.V. Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species. New J. Chem. 2022, 46, 12041–12053, doi: 10.1039/d2nj01828d.
  15. Danilkina, N.A.; Khmelevskaya, E.A.; Lyapunova, A.G.; D’yachenko, A.S.; Bunev, A.S.; Gasanov, R.E.; Gureev, M.A.; Balova, I.A. Functionalized 10-Membered Aza- and Oxaenediynes through the Nicholas Reaction. Molecules 2022, 27, 6071, doi: 10.3390/molecules27186071.
  16. Igushkina, A.V.; Golovanov, A.A.; Vasilyev, A.V. Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis. Molecules 2022, 27, 1256, doi: 10.3390/molecules27041256.
  17. Kritchenkov, I.S.; Mikhnevich, V.G.; Stashchak, V.S.; Solomatina, A.I.; Kozina, D.O.; Sokolov, V.V.; Tunik, S.P. Novel NIR-Phosphorescent Ir(III) Complexes: Synthesis, Characterization and Their Exploration as Lifetime-Based O2 Sensors in Living Cells. Molecules 2022, 27, 3156, doi: 10.3390/molecules27103156.
  18. Kalyaev, M.V.; Ryabukhin, D.S.; Borisova, M.A.; Ivanov, A.Y.; Boyarskaya, I.A.; Borovkova, K.E.; Nikiforova, L.R.; Salmova, J.V.; Ul’yanovskii, N.V.; Kosyakov, D.S.; Vasilyev, A.V. Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity. Molecules 2022, 27, 4612, doi: 10.3390/molecules27144612.
  19. Sakharov, P.A.; Rostovskii, N.V.; Khlebnikov, A.F.; Novikov, M.S. Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds. Molecules 2022, 27, 5681, doi: 10.3390/molecules27175681.
  20. Govdi, A.I.; Tokareva, P.V.; Rumyantsev, A.M.; Panov, M.S.; Stellmacher, J.; Alexiev, U.; Danilkina, N.A.; Balova, I.A. 4,5-Bis(arylethynyl)-1,2,3-triazoles — A New Class of Fluorescent Labels: Synthesis and Applications. Molecules 2022, 27, 3191, doi: 10.3390/molecules27103191.
  21. Gholinejad, M.; Shojafar, M.; Sansano, J.M.; Mikhaylov, V.N.; Balova, I.A.; Khezri, R. Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes. J. Organomet. Chem. 2022, 970–971, doi: 10.1016/j.jorganchem.2022.122359.
  22. Firsov, A.; Bakulina, O.; Dar’in, D.; Sokolov, V.V.; Krasavin, M. Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli–Cushman Reaction of Sultam-Based Dicarboxylic Acids. J. Org. Chem. 2022, 87, 1537–1540, doi: 10.1021/acs.joc.1c02456.
  23. Ilkin, V.G.; Filimonov, V.O.; Seliverstova, E.A.; Novikov, M.S.; Beryozkina, T.V.; Gagarin, A.A.; Belskaya, N.P.; Muthipeedika, N.J.; Bakulev, V.A.; Dehaen, W. Thioisomünchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds. J. Org. Chem. 2022, 87, 12196–12213, doi: 10.1021/acs.joc.2c01352.
  24. Filippov, I.P.; Agafonova, A.V.; Titov, G.D.; Smetanin, I.A.; Rostovskii, N.V.; Khlebnikov, A.F.; Novikov, M.S. Synthesis of Imidazo[1,2-a]pyridines via Near UV Light-Induced Cyclization of Azirinylpyridinium Salts. J. Org. Chem. 2022, 87, 6514–6519, doi: 10.1021/acs.joc.2c00514.
  25. Galenko, E.E.; Puzyk, A.M.; Novikov, M.S.; Khlebnikov, A.F. An Isoxazole Strategy for Molybdenum-Mediated Synthesis of 5-Mono- and 4,5-Disubstituted 1H-Pyrrole-2,3-diones. J. Org. Chem. 2022, 87, 6459–6470, doi: 10.1021/acs.joc.2c00386.
  26. Filippov, I.P.; Novikov, M.S.; Khlebnikov, A.F.; Rostovskii, N.V. One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds. J. Org. Chem. 2022, 87, 8835–8840, doi: 10.1021/acs.joc.2c00977.
  27. Kaminskiy, N.A.; Galenko, E.E.; Kryukova, M.A.; Novikov, M.S.; Khlebnikov, A.F. Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles. J. Org. Chem. 2022, 87, 10485–10492, doi: 10.1021/acs.joc.2c01102.
  28. Pankova, A.S. Two-Step Construction of Thiophene-Oxazole Dyads with Fluorescent Properties by the Ring Expansion of Aziridines. J. Org. Chem. 2022, 87, 11121–11130, doi: 10.1021/acs.joc.2c01365.
  29. Kartsova, L.A.; Moskvichev, D.O. In-Capillary Chiral Derivatization of Amino Acids. J. Anal. Chem. 2022, 77, 618–624, doi: 10.1134/S1061934822050057.
  30. Shmakov, S.V.; Latypova, D.K.; Shmakova, T.V.; Rubinshtein, A.A.; Chukin, M.V.; Zhuravskii, S.G.; Knyazev, N.A.; Stepakov, A.V.; Galagudza, M.M.; Boitsov, V.M. Biological Evaluation of 3-Azaspiro[Bicyclo[3.1.0]Hexane-2,5’-Pyrimidines] as Potential Antitumor Agents. Int. J. Mol. Sci. 2022, 23, 10759, doi: 10.3390/ijms231810759.
  31. Bakhtyukov, A.A.; Derkach, K. V; Sorokoumov, V.N.; Stepochkina, A.M.; Romanova, I. V; Morina, I.Y.; Zakharova, I.O.; Bayunova, L. V; Shpakov, A.O. The effects of separate and combined treatment of male rats with type 2 diabetes with metformin and orthosteric and allosteric agonists of luteinizing hormone receptor on steroidogenesis and spermatogenesis. Int. J. Mol. Sci. 2022, 23, 198, doi: 10.3390/ijms23010198.
  32. Borisova, M.A.; Ryabukhin, D.S.; Yu. Ivanov, A.; Boyarskaya, I.A.; Shabalin, D.A.; Zelenkov, L.E.; Yu. Schmidt, E.; Trofimov, B.A.; Vasilyev, A.V. Transformations of 5-Hydroxy-1-pyrrolines in Strong Brønsted Acids: Experimental and Theoretical Study of Intermediate Cationic Species. Eur. J. Org. Chem. 2022, 2022, e202200468, doi: 10.1002/ejoc.202200468.
  33. Bakhtyukov, A.A.; Derkach, K. V; Fokina, E.A.; Sorokoumov, V.N.; Zakharova, I.O.; Bayunova, L. V; Shpakov, A.O. Development of Low-Molecular-Weight Allosteric Agonist of Thyroid-Stimulating Hormone Receptor with Thyroidogenic Activity. Dokl. Biochem. Biophys. 2022, 503, 67–70, doi: 10.1134/S1607672922020016.
  34. Baykov, S.; Tarasenko, M.; Kotlyarova, V.; Shetnev, A.; Zelenkov, L.E.; Boyarskaya, I.A.; Boyarskiy, V.P. 2-(1,2,4-Oxadiazol-5-yl)aniline as a New Scaffold for Blue Luminescent Materials. ChemistrySelect 2022, 7, e202201201, doi: 10.1002/slct.202201201.
  35. Penney, A.A.; Efremova, M.M.; Molchanov, A.P.; Kryukova, M.A.; Kudinov, A.Y.; Bunev, A.S.; Keresten, V.M.; Kuznetsov, M.A. 1,3-Dipolar versus Nucleophilic Reactivity of Diaziridines Based on 3,4-Dihydroisoquinoline toward Aryl Iso(thio)cyanates. ChemistrySelect 2022, 7, e202202627, doi: 10.1002/slct.202202627.
  36. Derkach, K. V; Fokina, E.A.; Bakhtyukov, A.A.; Sorokoumov, V.N.; Stepochkina, A.M.; Zakharova, I.O.; Shpakov, A.O. The Study of Biological Activity of a New Thieno[2,3-d]-Pyrimidine-Based Neutral Antagonist of Thyrotropin Receptor. Bull. Exp. Biol. Med. 2022, 172, 713–717, doi: 10.1007/s10517-022-05462-x.
  37. Zharskaia, N.A.; Solomatina, A.I.; Liao, Y.-C.; Galenko, E.E.; Khlebnikov, A.F.; Chou, P.-T.; Chelushkin, P.S.; Tunik, S.P. Aggregation-Induced Ignition of Near-Infrared Phosphorescence of Non-Symmetric [Pt(C^N*N’^C’)] Complex in Poly(caprolactone)-based Block Copolymer Micelles: Evaluating the Alternative Design of Near-Infrared Oxygen Biosensors. Biosensors 2022, 12, 695, doi: 10.3390/bios12090695.
  38. Zanakhov, T.O.; Galenko, E.E.; Novikov, M.S.; Khlebnikov, A.F. An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydro-pyridine-3-carboxylates. Beilstein J. Org. Chem. 2022, 18, 738–745, doi: 10.3762/bjoc.18.74.
  39. Filatov, A.S.; Khoroshilova, O.V.; Larina, A.G.; Boitsov, V.M.; Stepakov, A.V. Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann’s purple. Beilstein J. Org. Chem. 2022, 18, 769–780, doi: 10.3762/bjoc.18.77.
  40. Kalinichev, A.V.; Kravchenko, A.V.; Gryazev, I.P.; Kechin, A.A.; Karpukhin, O.R.; Khairullina, E.M.; Kartsova, L.A.; Golovkina, A.G.; Kozynchenko, V.A.; Peshkova, M.A.; et al. Classification of ballpoint pen inks based on selective extraction and subsequent digital color and cluster analyses. Analyst 2022, 147, 3055–3064, doi: 10.1039/d2an00482h.
  41. Makeeva, D.V.; Antipova, K.S.; Kartsova, L.A. Electrophoretic determination of carboxylic acids in blood serum with intracapillary concentration. Anal. i Kontrol 2022, 26, 13–20, doi: 10.15826/analitika.2022.26.1.001.
  42. Zenkevich, I.G.; Derouiche, A.; Nikitina, D.A. Important features of retention indices determination in reversed-phase high performance liquid chromatography. Anal. i Kontrol 2022, 26, 57–63, doi: 10.15826/analitika.2022.26.1.007.
  43. Zenkevich, I.G.; Derouiche, A. Analytical aspects of organic compounds retention indice dependence in reversed phase HPLC on the content of methanol in eluent. Anal. i Kontrol 2022, 26, 41–48, doi: 10.15826/analitika.2022.26.1.004.
  44. Kasatkina, S.O.; Geyl, K.K.; Baykov, S.V.; Novikov, M.S.; Boyarskiy, V.P. “Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents. Adv. Synth. Catal. 2022, 364, 1295–1304, doi: 10.1002/adsc.202101490.
  45. Sakharov, P.A.; Novikov, M.S.; Nguyen, T.K.; Kinzhalov, M.A.; Khlebnikov, A.F.; Rostovskii, N.V. Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines. ACS Omega 2022, 7, 9071–9079, doi: 10.1021/acsomega.2c00367.
  46. Babushkina, A.A.; Mikhaylov, V.N.; Novikov, A.S.; Sorokoumov, V.N.; Gureev, M.A.; Kryukova, M.A.; Shpakov, A.O.; Balova, I.A. Synthesis , X-ray and DFT studies of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones. Chem. Heterocycl. Compd. 2022, 58, 432–437.
  47. Strashkov, D.M., Zavyalov, K.V., Sakharov, P.A., ...Khlebnikov, A.F., Novikov, M.S. Rhodium-catalyzed migrative annulation and olefination of 2-aroylpyrroles with diazoesters. Org. Chem. Front. 2022, 10, 506–513. DOI: 10.1039/D2QO01759H.
  48. Karcev, D.D., Efremova, M.M., Molchanov, A.P., ...Bunev, A.S., Khochenkov, D.A. Selective and Reversible 1,3-Dipolar Cycloaddition of 2-(2-Oxoindoline-3-ylidene)acetates with Nitrones in the Synthesis of Functionalized Spiroisoxazolidines. Int. J. Mol. Sci. 2022, 23, 12639. DOI: 10.3390/ijms232012639.