People

Nikolai V. Rostovskii

oh Rostovskiy NVORCID 0000-0002-8925-794X

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Phone 007-812-4289384

Publications

  1. 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, DOI: 10.1039/D0OB00693A.
  2. 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.
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
  31. 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
  32. 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
  33. 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
  34. 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
  35. 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
  36. 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
  37. 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
  38. 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