Organic Chemistry

RU

Publications in 2020

  1. Rostovskii N. V., Koronatov A. N., Sakharov P. A., Agafonova A. V., Novikov M. S., Khlebnikov A. F., Rogacheva, E. V., Kraeva, L.A., Azirine-containing dipeptides and depsipeptides: Synthesis, transformations and antibacterial activity. Org. Biomol. Chem. 2020, 18, 9448–9460. DOI: 10.1039/d0ob02023k.
  2. 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.
  3. Koronatov A. N., Rostovskii N. V., Khlebnikov A. F., Novikov M. S., Synthesis of 3-Alkoxy-4-Pyrrolin-2-ones via Rhodium(II)-Catalyzed Denitrogenative Transannulation of 1H-1,2,3-Triazoles with Diazo Esters. Org. Lett. 2020, 22, 7958−7963. DOI: 10.1021/acs.orglett.0c02893.
  4. Rashevskii A., Bakulina O., Novikov M. S., Dar'in D., Krasavin M., When periphery matters: Enhanced reactivity of 8-oxa-1,4-dithiaspiro[4.5]decane-7,9-dione and 9-oxa-1,5-dithiaspiro[5.5]undecane-8,10-dione in the Castagnoli-Cushman reaction with imines. Tetrahedron Lett. 2020, 61, 152658. DOI: 10.1016/j.tetlet.2020.152658.
  5. 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.
  6. Funt L. D., Krivolapova Y. 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.
  7. Galenko E. E., 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.
  8. 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 Applied Polymer Materials. 2020, 2, 537−547. DOI: 10.1021/acsapm.9b00952.
  9. Smetanin I. A., Agafonova A. V., Rostovskii N. V., Khlebnikov A. F., Yufit D. S., Novikov M. S., Stereoselective assembly of 3,4-epoxypyrrolines via nucleophilic addition induced domino cyclization of 6-halo-1-oxa-4-azahexatrienes. Org. Chem. Front. 2020, 7, 525−530. DOI: 10.1039/C9QO01401B.
  10. Sakharov P. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S., Regiodivergent Synthesis of Butenolide-Based α- And β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion. Org. Lett. 2020, 22, 3023−3027. DOI: 10.1021/acs.orglett.0c00793.
  11. Filippov I. P., Novikov M. S., Khlebnikov A. F., Rostovskii N. V., Pseudopericyclic Dearomative 1,6-Cyclization of 1-(2-Pyridyl)-2-azabuta-1,3-dienes: Synthesis and Ring–Chain Valence Equilibria of 4H-Pyrido[1,2-a]pyrazines. Eur. J. Org. Chem. 2020, 3688−3698. DOI: 10.1002/ejoc.202000210.
  12. Nguyen T. K., Titov G. D., Khoroshilova O. V., Kinzhalov M. A., Rostovskii N. V., Light-induced one-pot synthesis of pyrimidine derivatives from vinyl azides. Org. Biomol. Chem. 2020, 18, 4971–4982. DOI: 10.1039/D0OB00693A.
  13. Silaichev P. S., Beryozkina T. V., Novikov M. S., Dehaen W., Bakulev V. A., A Base-Controlled Reaction of 2-Cyanoacetamidines (3,3-Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4-Methylene-1,2,3-triazole-5-imines. Eur. J. Org. Chem. 2020, 2020, 3688−3698. DOI: 10.1002/ejoc.202000453
  14. 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
  15. Rostovskii N. V., Smetanin I. A., Koronatov A. N., Agafonova A. V., Potapenkov V. V., Khlebnikov A. F., Novikov M. S., Chem. Het. Comp. 2020, 56, 881–887, DOI: 10.1007/s10593-020-02745-x.
  16. 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. Het. Comp. 2020, 56, 875−880, DOI: 10.1007/s10593-020-02744-y.
  17. Filippov I. P., Titov G. D., Rostovskii N. V., Recent Advances in Denitrogenative Reactions of Pyridotriazoles. Synthesis 2020, 18, 3564–3576. DOI: 10.1055/s-0040-1707254.
  18. Danilkina N. A., Govdi A. I., Balova I. A., 5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks. Synthesis 2020, 52, 1874–1896. DOI: 10.1055/s-0039-1690858.
  19. Danilkina N. A., D’yachenko A. S., Govdi A. I., Khlebnikov A. F., Kornyakov I. V., Bräse, S., Balova, I. A. Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin. J. Org. Chem. 2020, 85, 9001–9014, DOI: 10.1021/acs.joc.0c00930.
  20. Danilkina N. A., Vasileva A. A., Balova I. A., A. E. Favorskii's scientific legacy in modern organic chemistry: Prototropic acetylene - Allene isomerization and the acetylene zipper reaction. Russ. Chem. Rev. 2020, 89, 125−171. DOI: 10.1070/RCR4902.
  21. Mikhaylov V. N., Sorokoumov V. N., Novikov A. S., Melnik M. V., Tskhovrebov A. G., Balova I. A., Intramolecular hydrogen bonding stabilizes trans-configuration in a mixed carbene/isocyanide PdII complexes. J. Organometallic Chem. 2020, 912, 121174. DOI: 10.1016/j.jorganchem.2020.121174.
  22. Gordeychuk D. I., Sorokoumov V. N., Mikhaylov V. N., Panov M. S., Khairullina E. M., Melnik M. V., Kochemirovsky V. A., Balova I. A., Copper-based nanocatalysts produced via laser-induced ex situ generation for homo- and cross-coupling reactions. Chem. Eng. Sci. 2020, 227, 115940. DOI: 10.1016/j.ces.2020.115940.
  23. Mikhaylov V. N., Pavlov A. O., Ogorodnov Y. V., Spiridonova D. V., Sorokoumov V. N., Balova I. A., N-Propargylation and Copper(I)-Catalyzed Azide-Alkyne Cycloaddition as a Convenient Strategy for Directed Post-Synthetic Modification of 4-Oxo-1,4-Dihydrocinnoline Derivatives. Chem. Het. Comp. 2020, 56, 915–922. DOI: 10.1007/s10593-020-02750-0
  24. Derkach K. V., Bakhtyukov A. A., Sorokoumov V. N., Shpakov A. O., New Thieno-[2,3-d]pyrimidine-Based Functional Antagonist for the Receptor of Thyroid Stimulating Hormone. Doklady Biochemistry And Biophysics, 2020, 491, 77–80. DOI: 10.1134/S1607672920020064.
  25. Bakhtyukov A. A., Derkach K. V., Gureev M. A., Dar’in D. V., Sorokoumov V. N., Romanova I. V., Morina I. Y., Stepochkina A. M., Shpakov A. O., Comparative study of the steroidogenic effects of human chorionic gonadotropin and thieno[2,3-d]pyrimidine-based allosteric agonist of luteinizing hormone receptor in young adult, aging and diabetic male rats. Int. J. Mol. Sci. 2020, 21, 1-28. DOI: 10.3390/ijms21207493.
  26. Molchanov A. P., Efremova M. M., Kryukova M. A., Kuznetsov M. A., Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation. Beilstein J. Org. Chem. 2020, 16, 2679–2686. DOI: 10.3762/BJOC.16.218.
  27. Sirotkina E. V., Efremova M. M., Starova G. L., Kuznetsov M. A., Molchanov A. P., Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. Chem. Het. Comp. 2020, 56, 1193-1201. DOI: 10.1007/s10593-020-02797-z.
  28. Molchanov A. P., Lukina V. M., Efremova M. M., Muryleva A. A., Slita A. V., Zarubaev V. V., The 1,3-dipolar cycloaddition of adamantine-derived nitrones with maleimides. Synth. Commun. 2020, 50, 1367−1374. DOI: 10.1080/00397911.2020.1738494.
  29. Mikherdov A. S., Katkova S. A., Novikov A. S., Efremova M. M., Reutskaya E. Y., Kinzhalov M. A., (Isocyano group)⋯lone pair interactions involving coordinated isocyanides: experimental, theoretical and CSD studies. CrystEngComm 2020, 22, 1154−1159. DOI: 10.1039/C9CE01741K.
  30. Efremova M. M., Molchanov A. P., Novikov A. S., Starova G. L., Muryleva A. A., Slita A. V., Zarubaev V. V., 1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation. Tetrahedron. 2020, 76, 131104. DOI: 10.1016/j.tet.2020.131104.
  31. Pankova A. S., Electrophile-Induced Reactions of Cross-Conjugated Enynones in the Synthesis of Heterocycles. Chem. Het. Comp. 2020, 56, 829−836. DOI: 10.1007/s10593-020-02739-9
  32. Kritchenkov I. S., Elistratova A. A., Sokolov V. V., Chelushkin P. S., Shirmanova M. V., Lukina M. M., Dudenkova V. V., Shcheslavskiy V. I., Kalinina S., Reeß K., Rück A., Tunik S. P., A biocompatible phosphorescent Ir(iii) oxygen sensor functionalized with oligo(ethylene glycol) groups: Synthesis, photophysics and application in PLIM experiments. New J. Chem. 2020, 44, 10459–10471. DOI: 10.1039/d0nj01405b.
  33. Shakirova J. R., Hendi Z., Zhukovsky D. D., Sokolov V. V., Jamali S., Pavlovskiy V. V., Porsev V. V., Evarestov R. A., Tunik S. P., Inorg. Chim. Acta 2020, 511, 119776. DOI: 10.1016/j.ica.2020.119776.
  34. Igushkina A. V., Golovanov A. A., Boyarskaya I. A., Kolesnikov I. E., Vasilyev A. V., Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA. Molecules, 2020, 25. DOI: 10.3390/molecules25245920
  35. Ismagilova A. R., Zakusilo D. N., Osetrova L. V., Vasilyev A. V., Reaction of 5-phenylpenta-2,4-dienoic acid with benzene in trifluoromethanesulfonic acid. Russ. Chem. Bull. 2020, 69, 1928-1932. DOI: 10.1007/s11172-020-2980-7.
  36. Zaitceva O., Louis B., Beneteau V., Pale P., Shanmugam S., Evstigneyev E. I., Vasiliev A. V., Post-modified FAU zeolites as efficient catalysts for the synthesis of coumarins. Catalysis Today, 2020, in press. DOI: 10.1016/j.cattod.2020.06.081.
  37. Zaitceva O. A., Beneteau V., Ryabukhin D. S., Louis B., Vasilyev A. V., Pale P., Zeolite-promoted synthesis of coumarins and thiocoumarins. ChemCatChem 2020, 12, 326−333. DOI: 10.1002/cctc.201901384.
  38. Zaitceva O. A., Beneteau V., Ryabukhin D. S., Eliseev I. I., Kinzhalov M. A., Louis B., Vasilyev A. V., Pale P., Cyclization of aryl 3-aryl propynoates into 4-arylcoumarines catalyzed by cyclometalated Platinum(II) complexes. Tetrahedron 2020, 76, 131029. DOI: 10.1016/j.tet.2020.131029.
  39. Khoroshilova O. V., Vasilyev A. V., Generation and NMR study of short-lived and reactive trifluoroalkyl carbocations of the α-halogenothiophene series in Brønsted superacids: reactions of the cations with arenes. J. Org. Chem. 2020, 85, 5872−5883. DOI: 10.1021/acs.joc.0c00170.
  40. Gorbunova Y., Zakusilo D. N., Boyarskaya I. A., Vasilyev A. V. Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones. Tetrahedron, 2020, 76, 131264. DOI: 10.1016/j.tet.2020.131264.
  41. Lozovskiy S. V., Vasilyev A. V., Catalyst-Free Preparation of Perfluoroalkyl-Phosphoryl Substituted Furans from 1-Perfluoroalkyl 1,3-Diketones in Two Steps. Adv. Synth. Catal., 2020, 362, 3121−3125. DOI: 10.1002/adsc.202000534.
  42. Borisova M. А., Ryabukhin D. S., Vasilyev, A. V., Reactions of quinoline-2(6,8)-carbaldehydes with arenes by the action of various Brønsted or Lewis acids: synthesis of diarylmethylquinolines. Chem. Het. Comp. 2020, 56, 964–967. DOI: 10.1007/s10593-020-02759-5.
  43. Zalivatskaya A. S., Golovanov A. А., Vasilyev A. V., Cyclization of 1-Aryl-5-Phenylpent-4-en-2-yn-1-Ones to 2,3-Dihydropyran-2-Ones in Trifluoromethanesulfonic Acid. Chem. Het. Comp. 2020, 56, 953–956. DOI: 10.1007/s10593-020-02756-8.
  44. Afanasenko A. M., Chulkova T. G., Boyarskaya I. A., Islamova R. M., Legin A. A., Keppler B. K., Selivanov S. I., Vereshchagin A. N., Elinson M. N., Haukka M., C,N-chelated diaminocarbene platinum(II) complexes derived from 3,4-diaryl-1H-pyrrol-2,5-diimines and cis-dichlorobis(isonitrile)platinum(II): Synthesis, cytotoxicity, and catalytic activity in hydrosilylation reactions. J. Organomet. Chem. 2020, 923, 121435. DOI: 10.1016/j.jorganchem.2020.121435
  45. Remizov Y. O., Kornev A. A., Pevzner L. M., Petrov M. L., Boitsov V. M., Stepakov A.V., In Vitro Activity of Organochalcogen Compounds: I. Cytotoxic Effect of 4-(1,2,3-Thiadiazol-4-yl)furans Against K562 and HeLa Tumor Cell Lines. Russ. J. Gen. Chem. 2020, 90, 2208–2213. DOI: 10.1134/S1070363220110328.
  46. Popova E. A., Kornev A. A., Shmakov S. V., Nepochatyi G. D., Kotyunina O. A., Petrov M. L., Boitsov V. M., Stepakov A. V., In Vitro Activity of Organochalcogen Compounds: II. Cytotoxic Effect of 2-Aminobenzo[b]thiophenes Against K562 and HeLa Tumor Cell Lines. Russ. J. Gen. Chem. 2020, 90, 2214–2218. DOI: 10.1134/S107036322011033X.
  47. Lenshmidt L. V., Ledovskaya M. S., Larina A. G., Filatov A. S., Chakchir O. B., Uspenskii A. A., Stepakov A. V., Synthesis of Isoxazolo[5',4':3,4]pyrrolo[1,2-a]azepines via N-Acyliminium Cyclization. Russ. J. Org. Chem. 2020, 56, 234–245. DOI: 10.1134/S1070428020020098.
  48. Selivanov S. I., Wang S., Filatov A. S., Stepakov A. V., NMR Study of Spatial Structure and Internal Dynamic of Adducts of Ninhydrin-Derived Azomethine Ylide with Cyclopropenes. Applied Magnetic Resonance 2020, 51, 165–182. DOI: 10.1007/s00723-019-01178-w.
  49. Stepanova O. V., Pevzner L. M., Petrov M. L., Stepanova N. P., Sokolova N. B., Stepakov, A. V., Synthesis of 4-(2-Fluoro-4-hydroxyphenyl)-1,2,3-thia- and -Selenadiazoles and Glycosides on Their Base. Russ. J. Gen. Chem. 2020, 90, 1241–1248. DOI: 10.1134/S1070363220070117
  50. Kartsova L. A., Makeeva D. V., Bessonova E. A., Current Status of Capillary Electrophoresis. J. Analyt. Chem. 2020, 75, 1497−1513. DOI: 10.1134/S1061934820120084.
  51. Kravchenko A., Kolobova E., Kartsova L., Multifunction covalent coatings for separation of amino acids, biogenic amines, steroid hormones, and ketoprofen enantiomers by capillary electrophoresis and capillary electrochromatography. SEPARATION SCIENCE PLUS 2020, 3, 102−111. DOI: 10.1002/sscp.201900098.
  52. Kartsova L., Moskvichev D., Bessonova E., Peshkova M. Imidazolium Ionic Liquids in Microemulsion Electrokinetic Chromatography for Separation of Polyphenol Antioxidants Chromatographia 2020, 83, 1001–1008. DOI: 10.1007/s10337-020-03921-z.
  53. Polikarpova D., Makeeva D., Kolotilina N., Dolgonosov A., Peshkova M., Kartsova L., Nanosized cation exchanger for the electrophoretic separation and preconcentration of catecholamines and amino acids. Electrophoresis 2020, 41, 1031−1038. DOI: 10.1002/elps.201900416.
  54. Makeeva D., Polikarpova D., Demyanova E., Roshchina E., Vakhitov T., Kartsova L., Determination of native amino acids and lactic acid in Lactobacillus helveticus culture media by capillary electrophoresis using Cu2+ and β-cyclodextrins as additives. J. Chromatogr. B 2020, 1156, 122304. DOI: 10.1016/j.jchromb.2020.122304.
  55. Deev V., Solovieva S., Andreev E., Protoshchak V., Karpushchenko E., Sleptsov A., Kartsova L., Bessonova E., Legin A., Kirsanov D., Prostate cancer screening using chemometric processing of GC–MS profiles obtained in the headspace above urine samples. J. Chromatogr. B 2020, 1155, 122298. DOI: 10.1016/j.jchromb.2020.122298.
  56. Bessonova E. A., Deev V. A., Kartsova L. A., Dispersive Liquid–Liquid Microextraction of Pesticides Using Ionic Liquids As Extractants. J. Analyt. Chem. 2020, 75, 991–999. DOI: 10.1134/S1061934820080043
  57. Tiuftiakov N. Y., Kalinichev A. V., Rudenko I. V., Bessonova E. A., Kartsova L. A., Peshkova M. A., pH-dependent distribution of the indicator dye tetrabromophenolphthalein ethyl ester between aqueous solution and plasticized polymeric phase: Predicting the lifetime of ion-selective optical sensors. Colloids and Interface Science Comm. 2020, 37, 100295. DOI: 10.1016/j.colcom.2020.100295.
  58. Shishov A., Gerasimov A., Nechaeva D., Volodina N., Bessonova E., Bulatov A., An effervescence-assisted dispersive liquid–liquid microextraction based on deep eutectic solvent decomposition: Determination of ketoprofen and diclofenac in liver. Microchem. J. 2020, 156, 104837. DOI: 10.1016/j.microc.2020.104837.
  59. Eliseenkov E. V., Zenkevich I. G., Characterization of Substituted 1,3-Dioxolanes and 1,3-Dioxanes by Gas Chromatography–Mass Spectrometry. J. Analyt. Chem. 2020, 75, 1790–1807. DOI: 10.1134/S1061934820140087
  60. Zenkevich I. G., Eliseenkov E. V., Principles of Controlling the Correctness of Gas-Chromatographic Retention Indices of Previously Uncharacterized Analytes (Based on an Example of 2-Aryl-1,3-Dioxolanes and 2-Aryl-1,3-Dioxanes). J. Analyt. Chem. 2020, 75, 1608–1625. DOI: 10.1134/S1061934820120151
  61. Zenkevich I. G., Specific Features of the Gas Chromatography–Mass Spectrometry Identification of Monoalkyl Phthalates. J. Analyt. Chem. 2020, 75, 1322–1329.
  62. Zenkevich I. G., Leleev E., Specific Features of the Gas Chromatographic Analysis of Samples in High-Boiling Solvents Using Capillary Columns with a Low Split Ratio of the Carrier Gas Flow. J. Analyt. Chem. 2020, 75, 73–83. DOI: 10.1134/S1061934820010165.
  63. Zenkevich I. G., Lukina V. M. Characteristic Features of the Gas Chromatographic Separation of Tautomers of Ethyl Acetoacetate. Russ. J. Phys. Chem. A 2020, 94, 1214–1223. DOI: 10.1134/S0036024420060357.
  64. Zenkevich I. G., Desyatova A. I., Modification of inertness test for gas chromatographic systems. Analitika i Kontrol 2020, 24, 133–141. DOI: 10.15826/analitika.2020.24.2.004.