People

RU

Nikolai V. Rostovskii

oh Rostovskiy NVORCID 0000-0002-8925-794X

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Phone 007-812-4289384

Publications

  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. Agafonova A. V., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S., Synthesis of 2-(2-Pyridyl)-2H-azirines via Metal-Free C–C Cross-Coupling of Bromoazirines with 2-Stannylpyridines. Org. Lett. 2021, DOI: 10.1021/acs.orglett.1c03060
  9. Rostovskii N. V., Novikov M. S., Khlebnikov A. F., Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes. Organics 2021, 2, 313–336. DOI: 10.3390/org2030017
  10. Tiuftiakov N. Y., Strelnikova J. O., Filippov I. P., Khaidarov A. R., Khlebnikov A. F., Bunev A. S., Novikov M. S., Rostovskii N. V., Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement. Org. Lett. 2021, 23, 6998–7002. DOI: 10.1021/acs.orglett.1c02706
  11. Golubev A. A., Agafonova A. V., Smetanin I. A., Rostovskii N. V., Khlebnikov A. F., Bunev A. S., Novikov M. S., A Hydroxypyrrole Approach to 2,2′-Bi(4-pyrrolin-3-ones) and Pyrrolone-Based α-Amino Esters. J. Org. Chem. 2021, 86, 10368–10379. DOI: 10.1021/acs.joc.1c01070
  12. Strelnikova J. O., Koronatov A. N., Rostovskii N. V., Khlebnikov A. F., Khoroshilova O. V., Kryukova, M. A., Novikov M. S., Rhodium-Catalyzed Denitrogenative Diazole-Triazole Coupling toward Aza-Bridged Structures and Imidazole-Based Chelating Ligands. Org. Lett. 2021, 23, 4173–4178. DOI: 10.1021/acs.orglett.1c01092
  13. Sakharov P. А., Novikov M. S., Rostovskii N. V., 2H-Azirines in medicinal chemistry. Chem. Heterocycl. Compd. 2021, 57, 512–521. DOI: 10.1007/s10593-021-02934-2
  14. Koronatov A. N., Afanaseva K. K., Sakharov P. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S., Rh(II)-Catalyzed denitrogenative 1-sulfonyl-1,2,3-Triazole-1-Alkyl-1,2,3-Triazole cross-coupling as a route to 3-sulfonamido-1H-pyrroles and 1,2,3-Triazol-3-ium ylides. Org. Chem. Front. 2021, 8, 1474–1481. DOI: 10.1039/D0QO01571G
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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.
  21. 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.
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
  31. 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
  32. 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
  33. 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
  34. 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
  35. 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
  36. 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
  37. 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
  38. 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
  39. 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
  40. 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
  41. 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
  42. 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
  43. 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
  44. 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
  45. 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
  46. 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
  47. 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
  48. 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
  49. 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
  50. 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
  51. 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
  52. 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
  53. 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
  54. 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
  55. 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
  56. 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
  57. 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