Organic Chemistry

RU

Publications in 2023

  1. Agafonova A. V., Golubev A. A., Smetanin I. A., Khlebnikov A. F., Spiridonova D. V., Novikov M. S. Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C–N or C–C Azirine Bond in 2-Pyridylazirines. Org. Lett. 2023, DOI: 10.1021/acs.orglett.3c02696
  2. Mammeri O. A., Baranov I. M., Ivanov A. Yu., Boyarskaya I. A., Vasilyev A. V. Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid. Tetrahedron 2023, 146, 133649. DOI: 10.1016/j.tet.2023.133649
  3. Il’in, M.V., Polonnikov, D.A., Novikov, A.S., Sysoeva, A.A., Safinskaya, Y.V., Bolotin, D.S. Influence of Coordination to Silver(I) Centers on the Activity of Heterocyclic Iodonium Salts Serving as Halogen-Bond-Donating Catalysts. ChemPlusChem 2023, e202300304. DOI: 10.1002/cplu.202300304
  4. Pankova, A.S., Golubev, P., Molin, I.A., Rostovskii, N.V. Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. Eur. J. Org. Chem. 2023, 26, e202300573. DOI: 10.1002/ejoc.202300573
  5. Vidyakina, A.A., Shtyrov, A.A., Ryazantsev, M.N., Khlebnikov, A. F., Kolesnikov, I. E., Sharoyko, V. V., Spiridonova, D. V., Balova, I. A., Bräse, S., Danilkina, N.A. Development of Fluorescent Isocoumarin-Fused Oxacyclononyne – 1,2,3-Triazole Pairs. Chem. Eur. J. 2023, 29, e202300540. DOI: 10.1002/chem.202300540
  6. Galenko, E.E., Novikov, M.S., Khlebnikov, A.F. [2 + 2] Cycloaddition/Retro-Electrocyclization/Decarboxylation Reaction Sequence: Access to 4-Aminopyridines from Methylideneisoxazolones and Ynamines. J. Org. Chem. 2023, 88, 8854–8864. DOI: 10.1021/acs.joc.3c00654
  7. Silaichev, P.S., Beryozkina, T.V., Ilkin, V., Novikov, M.S., Dehaen, W., Bakulev, V.A. Tandem Cycloaddition of Azides to 3,3-Diaminoacrylonitriles (2-Cyanoacetamidines) and Cornforth-Type Rearrangement as an Approach to 5-Amino-1,2,3-triazole-4-N-substituted Imidamides. J. Org. Chem. 2023, 88, 8163–8174. DOI: 10.1021/acs.joc.3c00151
  8. Vasilchenko, D.S., Agafonova, A.V., Simdianov, I.V., Koronatov, A. N., Sakharov, P.A., Romanenko, I. A., Rostovskii, N.V., Khlebnikov, A.F., Novikov, M.S. 2H-1,2,3-triazole-4-carboxylic acids via Ru(II)-catalyzed rearrangement of 4-hydrazonoisoxazol-5-ones. Tetrahedron Lett. 2023, 123, 154580. DOI: 10.1016/j.tetlet.2023.154580
  9. Zakharov, T.N., Sakharov, P.A., Novikov, M.S., Khlebnikov, A.F., Rostovskii, N.V. Triethylamine-Promoted Oxidative Cyclodimerization of 2H-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study. Molecules 2023, 28, 4315. DOI: 10.3390/molecules28114315
  10. Taishev, A.E., Galenko, E.E., Novikov, M.S., Khlebnikov, A.F. Simple Access to Isoxazole-Containing Heterocyclic Hybrids: Isoxazole/Oxazole and Isoxazole/Pyridine. Russ. J. Gen. Chem. 2023, 93, 1246–1260. DOI: 10.1134/s1070363223050250
  11. Titov, G.D., Antonychev, G.I., Novikov, M.S., Khlebnikov, A.F., Rogacheva, E. V., Kraeva, L.A., Rostovskii, N.V. Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids. Org. Lett. 2023, 25, 2707–2712. DOI: 10.1021/acs.orglett.3c00823
  12. Galenko, E.E., Zanakhov, T.O., Novikov, M.S., Khlebnikov, A.F. Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: synthesis of fully substituted pyrimidines. Org. Biomol. Chem. 2023, 21, 2990–3001. DOI: 10.1039/D3OB00148B
  13. Galenko, E.E., Zanakhov, T.O., Novikov, M.S., Khlebnikov, A.F. Pd-catalyzed heteroannulation of isoxazoles: Convergent synthesis of isoxazolo[5,4-c]quinolones. Tetrahedron Lett. 2023, 114, 154270. DOI: 10.1016/j.tetlet.2022.154270
  14. Agafonova, A.V., Novikov, M.S., Khlebnikov, A.F. 5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids. Molecules 2023, 28, 275. DOI: 10.3390/molecules28010275
  15. Govdi, A.I., Anisimov, S.O., Danilkina, N.A., Bunev, A.S., Balova, I.A. Acyclic enediynes fused to triazole and benzothiophene containing propargylamine moieties. Mendeleev Commun. 2023, 33, 328–330. DOI: 10.1016/j.mencom.2023.04.010
  16. Babushkina, A.A., Mikhailov, V.N., Ogurtsova, A.D., Bunev, A. S., Sorokoumov, V.N., Balova, I.A. The Richter reaction in the synthesis of combretastatin analogs. Russ. Chem. Bull. 2023, 72, 1012–1022. DOI: 10.1007/s11172-023-3866-3
  17. Derkach, K.V., Gureev, M.A., Babushkina, A.A., Mikhaylov, V.N., Zakharova, I.O., Bakhtyukov, A.A., Sorokoumov, V.N., Novikov, A.S., Krasavin, M., Shpakov, A.O., Balova, I.A. Dual PTP1B/TC-PTP Inhibitors: Biological Evaluation of 3-(Hydroxymethyl)cinnoline-4(1H)-Ones. Int. J. Mol. Sci. 2023, 24, 4498. DOI: 10.3390/ijms24054498
  18. Efremova, M.M., Rumyantsev, A.M., Babitova, E.S., Ianshina, T.M., Govdi, A.I. Synthesis of 5-ethynylisoxazoles based on 1,3-dipolar cycloaddition reactions of nitrile oxides with conjugated diynes. Russ. Chem. Bull. 2023, 72, 1717–1721. DOI: 10.1007/s11172-023-3952-5
  19. Cells Ianshina, T., Sidorin, A., Petrova, K., Shubert, M., Makeeva, A., Sambuk, E., Govdi, A., Rumyantsev, A., Padkina, M. Effect of Methionine on Gene Expression in Komagataella phaffii. Microorganisms 2023, 11, 877. DOI: 10.3390/microorganisms11040877
  20. Sokolov, A.A., Egorov, D.M., Pronina, Y.A., Ramsh, S.M., Stepakov, A.V. 1,3-Dipolar Cycloaddition of Stable Azomethine Ylide Based on Ninhydrin and L-Proline to Phosphorylated Acetylenes. Russ. J. Gen. Chem. 2023, 93, 1694–1699. DOI: 10.1134/S1070363223070083
  21. Pevzner, L.M., Makhneva, E.A., Shmakov, S.V., Petrov, M.L., Stepakov, A.V., Boitsov, V.M. In Vitro Activity of Organochalcogen Compounds: IV. Synthesis and Cytotoxic Effect of 4-(1,2,3-Thiadiazol-4-yl)furans Against HeLa, Sk-mel-2, and B16 Tumor Cell Lines. Russ. J. Gen. Chem. 2023, 93, 1513–1522. DOI: 10.1134/S1070363223060245
  22. Pevzner, L.M., Ostrovskaya, A.A., Petrov, M.L., Stepakov, A.V. Synthesis of Ethyl 2-Methyl-4-(diethoxyphosphoryl)-4,7-dihydro-5H-thiopyrano[3,4-b]furan-5-carboxylate and Its Functionalization at the Position 3. Russ. J. Gen. Chem. 2023, 93, 827–840. DOI: 10.1134/S1070363223040084
  23. Pronina, Y.A., Stepakov, A.V., Popova, E.A., Boitsov, V.M., Baichurin, R.I., Selivanov, S.I. Diastereomers of Cyclopropa[a]pyrrolizine Spiro-fused with a Benzo[4,5]imidazo[1,2-a]indole Fragment: Structure Determinations Using NMR Methods. Appl. Magn. Reson. 2023 DOI: 10.1007/s00723-023-01608-w
  24. Komolova, D.D., Pronina, Y.A., Lozovskiy, S.V., Selivanov, S.I., Ponyaev, A.I., Filatov, A.S., Boitsov, V.M., Stepakov, A.V. Palladium-Catalyzed Oxidative Cycloaddition of Quinazoline-2,4(1H,3H)-diones and Diarylalkynes via C-H/N-H Activation. Synthesis 2023 DOI: 10.1055/a-2105-2850
  25. Makeeva, D.V., Antipova, K.S., Solovyeva, E.V., Morgacheva, V.P., Kolobova, E.A., Kartsova, L.A. Multilayer Coatings Based On Citrate-Stabilized Gold Nanoparticles and Polydiallyldimethylammonium Chloride for the Electrophoretic Separation of Carboxylic Acids. J. Anal. Chem. 2023, 78, 361–371. DOI: 10.1134/S1061934823030085
  26. Kartsova, L.A., Maliushevska, A.V., Kolobova, E.A. Analytical Capabilities of the Determination of Carbohydrates by Chromatographic and Electrophoretic Methods. J. Anal. Chem. 2023, 78, 144–161. DOI: 10.1134/S1061934823020041
  27. Karpitskiy, D.A., Bessonova, E.A., Shishov, A.Y., Kartsova, L.A. Selective extraction of plant bioactive compounds with deep eutectic solvents: Iris sibirica L. as example. Phytochem. Anal. 2023 DOI: 10.1002/pca.3272
  28. Kravchenko, A.V., Kolobova, E.A., Kechin, A.A., Kartsova, L.A. Development of a capillary electrophoretic method for determination of ketorolac enantiomers in human plasma using cationic β-cyclodextrin derivative as a chiral selector. J. Sep. Sci. 2023, 46, 2200601. DOI: 10.1002/jssc.202200601
  29. Zakusilo, D.N., Evstigneyev, E.I., Ivanov, A.Y., Mazur, A.S., Bessonova, E.A., Mammeri, O.A., Vasilyev, A.V. Structure of oxidized hydrolysis lignin. J. Wood Chem. Technol. 2023, 43, 103–115. DOI: 10.1080/02773813.2023.2187064
  30. Zenkevich, I.G. Linear Correlations of the Gas Chromatographic Retention Indices of Compounds from Various Taxonomic Groups. J. Anal. Chem. 2023, 78, 766–775. DOI: 10.1134/S1061934823040160
  31. Zenkevich, I.G., Deruish, A., Nikitina, D.A. Features of the Dependence of the Retention Indices of Sorbates in Reversed-Phase High-Performance Liquid Chromatography on the Content of Organic Solvents in the Eluent. Russ. J. Phys. Chem. A 2023, 97, 1007–1017. DOI: 10.1134/S0036024423050321
  32. Deruish, A., Karakashev, G.V., Ukolov, A.I., Zenkevich, I.G. Hydrolytic Stability of Unsubstituted Hydrazones of Aromatic Carbonyl Compounds in Reversed-Phase HPLC. J. Anal. Chem. 2023, 78, 222–230. DOI: 10.1134/S106193482302003X
  33. Savina, I.A., Gusev, D.M., Zimina, T.V., Golovanov, A.A., Zenkevich, I.G. Comparison of Gas-Chromatographic Retention Parameters of Aliphatic Enyne Alcohols with the Data for Their Structural Analogues. J. Anal. Chem. 2023, 78, 74–81. DOI: 10.1134/s1061934822120139
  34. Zenkevich, I.G., Baranov, D.A. Gas-Chromatographic Identification of Unusual Unstable Products of the Partial Hydrolysis of Tetraethoxysilane. J. Anal. Chem. 2023, 78, 82–90. DOI: 10.1134/S1061934823010148
  35. Zenkevich, I.G., Derouiche, A., Nikitina, D.A. Evidence for the Hydration of Some Organic Compounds during Reverse-Phase HPLC Analysis. Molecules 2023, 28, 734. DOI: 10.3390/molecules28020734
  36. Ignatova, I.I., Khoroshilova, O.V., Vasilyev, A.V. Aluminium trichloride-promoted tandem hydroarylation–ionic hydrogenation of 3-arylpropynoic acid derivatives and 4-phenylbut-3-yn-2-one. Mendeleev Commun. 2023, 33, 27–29. DOI: 10.1016/j.mencom.2023.01.008
  37. Samandarsangari, M., Kozina, D.O., Sokolov, V.V., Komarova, A.D., Shirmanova, M.V., Kritchenkov, I.S., Tunik, S.P. Biocompatible Phosphorescent O2 Sensors Based on Ir(III) Complexes for In Vivo Hypoxia Imaging. Biosensors 2023, 13, 680. DOI: 10.3390/bios13070680
  38. Novichikhina, N.P., Pantykina, D.A., Shestakov, A.S., Potapov, A.Yu., Ledenyova, I.V., Kuznetsov, M.A., Shikhaliev, K.S. Allylic and Retro-Allylic Rearrangements upon Bromination of 8,9-Substituted 4,4,6-Trimethyl-4H-Pyrrolo[3,2,1-ij]Quinoline-1,2-Diones. New Aspects and Synthetic Applications. ChemistrySelect 2023, 8, e202203981. DOI: 10.1002/slct.202203981
  39. Solovyeva, E.V., Odintsova, O.V., Svinko, V.O., Makeeva, D.V., Danilov, D.V. Hydroxyapatite-nanosilver composites with plasmonic properties for application in surface-enhanced Raman spectroscopy. Mater. Today Commun. 2023, 35, 105908. DOI: 10.1016/j.mtcomm.2023.105908
  40. Vasilchenko, D.S., Novikov, M.S., Rostovskii, N.V. Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines. Chem. Heterocycl. Compd. 2023, 59, 666-671. DOI: 10.1007/s10593-023-03252-5
  41. Pankova, A.S., Golubev, P., Molin, I.A., Rostovskii, N.V. Regioselective Synthesis of 2-Trimethylsilyl-4H-pyran-4-ones from 1-Ethoxy(hydroxy)-5-(trimethylsilyl)pentenynones. Eur. J. Org. Chem. 2023, 26, e202300573. DOI: 10.1002/ejoc.202300573
  42. Vasilchenko, D.S., Agafonova, A.V., Simdianov, I.V., Koronatov, A. N., Sakharov, P.A., Romanenko, I. A., Rostovskii, N.V., Khlebnikov, A.F., Novikov, M.S. 2H-1,2,3-triazole-4-carboxylic acids via Ru(II)-catalyzed rearrangement of 4-hydrazonoisoxazol-5-ones. Tetrahedron Lett. 2023, 123, 154580. DOI: 10.1016/j.tetlet.2023.154580
  43. Zakharov, T.N., Sakharov, P.A., Novikov, M.S., Khlebnikov, A.F., Rostovskii, N.V. Triethylamine-Promoted Oxidative Cyclodimerization of 2H-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study. Molecules 2023, 28, 4315. DOI: 10.3390/molecules28114315
  44. Titov, G.D., Antonychev, G.I., Novikov, M.S., Khlebnikov, A.F., Rogacheva, E. V., Kraeva, L.A., Rostovskii, N.V. Gold vs Light: Chemodivergent Reactivity of Diazoesters toward 2H-Azirine-2-carboxylic Acids. Org. Lett. 2023, 25, 2707–2712. DOI: 10.1021/acs.orglett.3c00823
  45. 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
  46. 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