People

Nikolai V. Rostovskii

oh Rostovskiy NVORCID 0000-0002-8925-794X

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Phone 007-812-4289384

Publications

  1. Strelnikova J. O., Rostovskii N. V., Khoroshilova O. V., Khlebnikov A. F., Novikov M. S., An Efficient Synthesis of Functionalized 2H-1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage. Synthesis 2021, 53, 348–358. DOI: 10.1055/s-0040-1707278
  2. 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
  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. Filippov I. P., Titov G. D., Rostovskii N. V., Recent Advances in Denitrogenative Reactions of Pyridotriazoles. Synthesis 2020, 52, 3564–3576. DOI: 10.1055/s-0040-1707254
  5. Rostovskii N. V., Smetanin I. A., Koronatov A. N., Agafonova A. V., Potapenkov V. V., Khlebnikov A. F., Novikov M. S., Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones. Chem. Heterocycl. Compd. 2020, 56, 881–887. DOI: 10.1007/s10593-020-02745-x
  6. 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.
  7. 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.
  8. 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, 2020, 3688−3698. DOI: 10.1002/ejoc.202000210
  9. I.A. Smetanin, A.V. Agafonova, N.V. Rostovskii, A.F. Khlebnikov, D.S. Yufit, M.S. Novikov 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. P.A. Sakharov, A.N. Koronatov, A.F. Khlebnikov, M.S. Novikov, A.G. Glukharev, E.V. Rogacheva, L.A. Kraeva, V.V. Sharoyko, T.B. Tennikova, N.V. Rostovskii Non-natural 2H-azirine-2-carboxylic acids: anexpedient synthesis and antimicrobial activity, RSC Adv., 2019, 9, 37901-37905. DOI: 10.1039/C9RA09345A
  11. A.N. Koronatov, N.V. Rostovskii, A.F. Khlebnikov, M.S. Novikov One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines. Chem. Heterocycl. Compd. 2019, 55, 1185–1189. DOI: 10.1007/s10593-019-02599-y
  12. A.V. Agafonova, I.A. Smetanin, N.V. Rostovskii, A.F. Khlebnikov, M.S. Novikov Easy Access to 2-Fluoro- and 2-Iodo-2H-azirines via the Halex Reaction. Synthesis 2019, 51, 4582-4589. DOI: 10.1055/s-0039-1690200
  13. A.A. Golubev, I.A. Smetanin, A.V. Agafonova, N.V. Rostovskii, A.F. Khlebnikov, G.L. Starova, M.S. Novikov [2 + 1 + 1] Assembly of spiro β-lactams by Rh(ii)-catalyzed reaction of diazocarbonyl compounds with azirines/isoxazoles. Org. Biomol. Chem., 2019, 17, 6821-6830. DOI: 10.1039/C9OB01301F
  14. P.A. Sakharov, N.V. Rostovskii, A.F. Khlebnikov, O.V. Khoroshilova, M.S. Novikov Transition Metal‐Catalyzed Synthesis of 3‐Coumaranone‐Containing NH‐Aziridines from 2H‐Azirines: Nickel(II) versus Gold(I). Adv. Synth. Catal. 2019, DOI: 10.1002/adsc.201900366
  15. P.A. Sakharov, N.V. Rostovskii, A.F. Khlebnikov, T.L. Panikorovskii, M.S. Novikov 2H‑Azirines as C−C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2‑c]quinolone Derivatives. Org. Lett. 2019, 21, 3615–3619. DOI: 10.1021/acs.orglett.9b01043
  16. A.R. Khaidarov, N.V. Rostovskii, A.A. Zolotarev, A.F. Khlebnikov, M.S. Novikov Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2H-Azirines with α-Imino Rh(II) Carbenoids. J. Org. Chem. 2019, 84, 3743–3753. DOI: 10.1021/acs.joc.8b03205
  17. A.F. Khlebnikov, M.S. Novikov, N.V. Rostovskii Advances in 2H-azirine chemistry: A seven-year update. Tetrahedron 2019, 75, 2555−2624. DOI: 10.1016/j.tet.2019.03.040
  18. A. R. Khaidarov, N. V. Rostovskii, G. L. Starova, A. F. Khlebnikov, M. S. Novikov Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles. Chem. Heterocycl. Compd. 2018, 54, 946–950. DOI: 10.1007/s10593-018-2378-8
  19. A. V. Agafonova, N. V. Rostovskii, I. A. Smetanin, G. L. Starova, A. F. Khlebnikov, M. S. Novikov Synthesis of 2-(Di/tri/tetraazolyl)-2H-azirine-2-carboxylates by Halogen Substitution: Evidence for an SN2′-SN2′ Cascade Mechanism. J. Org. Chem., 2018, 83, 13473–13480. DOI: 10.1021/acs.joc.8b02295
  20. A. V. Agafonova, I. A. Smetanin, N. V. Rostovskii, A. F. Khlebnikov, M. S. Novikov Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives. Org. Chem. Front., 2018, 5, 3396–3401. DOI: 10.1039/c8qo00982a
  21. J. O. Strelnikova, N. V. Rostovskii, G. L. Starova, A. F. Khlebnikov, M. S. Novikov Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles. J. Org. Chem., 2018, 83, 11232–11244. DOI: 10.1021/acs.joc.8b01809
  22. A. N. Koronatov, N. V. Rostovskii, A. F. Khlebnikov, M. S. Novikov Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines. J. Org. Chem. 2018, 83, 9210–9219. DOI: 10.1021/acs.joc.8b01228
  23. N. V. Rostovskii, I. A. Smetanin, A. V. Agafonova, P. A. Sakharov, J. O. Ruvinskaya, A. F. Khlebnikov, M. S. Novikov Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2H-azirines via an SN2′–SN2′ cascade in 2-halo-2H-azirines. Org. Biomol. Chem. 2018, 16, 3248–3257. DOI: 10.1039/C8OB00553B
  24. J. O. Ruvinskaya, N. V. Rostovskii, I. P. Filippov, A. F. Khlebnikov, M. S. Novikov A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(II) catalysis. Org. Biomol. Chem. 2018, 16, 38–42. DOI: 10.1039/c7ob02637d
  25. M. S. Novikov, N. V. Rostovskii, A. N. Koronatov, K. V. Zavyalov, G. V. Zubakin, A. F. Khlebnikov, G. L. Starova Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines. J. Org. Chem. 2017, 82, 13396−13404. DOI: 10.1021/acs.joc.7b02484
  26. A.V. Agafonova, I. A. Smetanin, N. V. Rostovskii, A. F. Khlebnikov, M. S. Novikov Synthesis of 2-halo-2Н-azirine-2-carboxylic acid amides and esters by isomerization of 5-(dialkylamino/alkoxy)-substituted isoxazoles, catalyzed by iron(II) sulfate. Chem. Heterocycl. Comp. 2017, 53, 1068–1071. DOI: 10.1007/s10593-017-2172-z
  27. N. V. Rostovskii, M. S. Novikov, A. F. Khlebnikov, D. S. Yufit Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetatecatalyzed Wolff rearrangement. Chem. Heterocycl. Comp. 2017, 53, 985–988. DOI: 10.1007/s10593-017-2160-3
  28. K. V. Zavyalov, M. S. Novikov, А. F. Khlebnikov, N. V. Rostovskii, G. L. Starova Rh2(OAc)4-Сatalyzed Reaction of 2-(2-Carbonylvinyl)-3-phenyl-2Н-azirines with Diazo Esters. Russ. J. Org. Chem. 2017, 53, 1214–1221. DOI: 10.1134/S1070428017080097
  29. N. V. Rostovskii, A. V. Agafonova, I. A. Smetanin, M. S. Novikov, A. F. Khlebnikov, J. O. Ruvinskaya, G. L. Starova Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2H-azirines. Synthesis 2017, 49, 4478–4488. DOI: 10.1055/s-0036-1590822
  30. P. A. Sakharov, N. V. Rostovskii, A. F. Khlebnikov, M. S. Novikov Annulation of five-membered cyclic enols with 3-aryl-2H-azirines: Catalytic versus non-catalytic cycloaddition. Tetrahedron 2017, 73, 4663–4670. DOI: 10.1016/j.tet.2017.06.037
  31. A. A. Melekhova, A. S. Novikov, N. V. Rostovskii, P. A. Sakharov, T. L. Panikorovskii, N. A. Bokach Open-chain hemiketal is stabilized by coordination to a copper (II). Inorg. Chem. Commun. 2017, 79, 82–85. DOI: 10.1016/j.inoche.2017.03.024
  32. N. V. Rostovskii, J. O. Ruvinskaya, M. S. Novikov, A. F. Khlebnikov, I. A. Smetanin, A. V. Agafonova Switchable Synthesis of Pyrroles and Pyrazines via Rh(II)-Catalyzed Reaction of 1,2,3-Triazoles with Isoxazoles: Experimental and DFT Evidence for the 1,4-Diazahexatriene Intermediate. J. Org. Chem. 2017, 82, 256−268. DOI: 10.1021/acs.joc.6b02389
  33. K.V. Zavyalov, M.S. Novikov, A.F. Khlebnikov, N.V. Rostovskii (3Z)-2-Azahexa-1,3,5-trienes: Generation and Regioselectivity of 1,5- and 1,6-Cyclizations. Russ. J. Org. Chem. 2016, 52, 1851–1853. DOI: 10.1134/S1070428016120265
  34. I. A. Smetanin, M. S. Novikov, A. V. Agafonova, N. V. Rostovskii, A. F. Khlebnikov, I. V. Kudryavtsev, M. A. Terpilowski, M. K. Serebriakova, A. S. Trulioff, N. V. Goncharov. A novel strategy for the synthesis of thermally stable and apoptosis-inducing 2,3-dihydroazetes. Org. Biomol. Chem. 2016, 14, 4479–4487. DOI: 10.1039/C6OB00588H
  35. M. S. Novikov, A. F. Khlebnikov, N. V. Rostovskii, S. Tcyrulnikov, A. A. Suhanova, K. V. Zavyalov, D. S. Yufit. Pseudopericyclic 1,5- versus pericyclic 1,4- and 1,6-electrocyclization in electron-poor 4-aryl-2-azabuta-1,3-dienes. Indole synthesis from 2H-azirines and diazo compounds. J. Org. Chem. 2015, 80, 18–29. DOI: 10.1021/jo501051n
  36. N. V. Rostovskii, M. S. Novikov, A. F. Khlebnikov, G. L. Starova, M. S. Avdontseva. Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization. Beilstein J. Org. Chem. 2015, 11, 302–312. DOI: 10.3762/bjoc.11.35
  37. A. V. Galenko, A. F. Khlebnikov, M. S. Novikov, V. V. Pakalnis, N. V. Rostovskii. Recent advances in isoxazole chemistry. Russ. Chem. Rev. 2015, 84, 335–377. DOI: 10.1070/RCR4503
  38. I. A. Smetanin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, G. L. Starova, D. S. Yufit. 4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2-halo-2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles. Tetrahedron 2015, 71, 4616–4628. DOI: 10.1016/j.tet.2015.05.022
  39. N. V. Rostovskii, P. A. Sakharov, M. S. Novikov, A. F. Khlebnikov, G. L. Starova. Cu(I)-NHC-Catalyzed (2+3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles. Org. Lett. 2015, 17, 4148–4151. DOI: 10.1021/acs.orglett.5b01883
  40. N. V. Rostovskii, M. S. Novikov, A. F. Khlebnikov, V. A. Khlebnikov, S. M. Korneev. Rh(II)-carbenoid mediated 2H-azirine ring-expansion as a convenient route to non-fused photo- and thermochromic 2H-1,4-oxazines. Tetrahedron 2013, 69, 4292–4301. DOI: 10.1016/j.tet.2013.03.106
  41. N. V. Rostovskii, M. S. Novikov, A. F. Khlebnikov, S. M. Korneev, D. S. Yufit. Cu(II)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles. Org. Biomol. Chem. 2013, 11, 5535–5545. DOI: 10.1039/c3ob40708j
  42. M. S. Novikov, I. A. Smetanin, A. F. Khlebnikov, N. V. Rostovskii, D. S. Yufit. Synthesis of electron-poor 4-halo-2-azabuta-1,3-dienes by Rh(II)-catalyzed diazo ester-azirine coupling. 2-Azabuta-1,3-diene-2,3-dihydroazete valence isomerism. Tetrahedron Lett. 2012, 53, 5777–5780. DOI: 10.1016/j.tetlet.2012.08.063
  43. V. A. Khlebnikov, M. S. Novikov, A. F. Khlebnikov, N. V. Rostovskii. Rh(II)-Catalyzed reactions of 2H-azirines with ethyl 2-acyl-2-diazoacetates. Synthesis of novel photochromic oxazines. Tetrahedron Lett. 2009, 50, 6509–6511. DOI 10.1016/j.tetlet.2009.09.033