Department of Organic Chemistry, lab #4231

Chemistry of Azapolyene and Ylide Intermediates

Short URL for media go.spbu.ru/rgnovikov

General Fields of Research Projects

  • Chemistry of N-, N,N- and N,O-heterocycles
  • Experimental and computational study of reaction mechanisms
  • Synthesis and applications of azapolyene compounds
  • New synthetic methodologies based on the reactions of carbenoids and nitrenoids

Tel. 007-812-4289344

Group members

oh Novikov MSGroup leader – Novikov Mikhail Sergeevich, Dr. Sc., professor.

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ORCID 0000-0001-5106-4723

Members

Research Projects

Highly functionalized azapolyenes: synthesis and applications in heterocyclic chemistry

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Synthesis of new N,O- и N,N-heterocyclic systems with useful photo-, thermo- and vapor-chromic properties

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Chemistry of fluorinated nitrogen ylides

nov3


New synthetic methods based on the reactions of carbenoids

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New synthetic methods based on the reactions of nitrenoids

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Experimental and computational study of pericyclic and pseudopericyclic reactions

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Publications 2011-2017

  1. Rostovskii N.V., Agafonova A.V., Smetanin I.A., Novikov M.S., Khlebnikov A.F., Ruvinskaya J.O., Starova G.L. “Metal-catalyzed isomerization of 5-heteroatom-substituted isoxazoles as a new roite to 2-halo-2H-azirines” Synthesis 2017, 49, 4478. DOI:.org/10.1016/j.tet.2017.06.037
  2. Zavyalov K.V., Novikov M.S., Khlebnikov A.F., Rostovskii N.V., Starova G.L. “Rh2(OAc)4-Сatalyzed reaction of 2-(2-carbonylvinyl)-3-phenyl-2Н-azirines with diazo esters” Russ. J. Org. Chem. 2017, 53, 1214. DOI: 10.1134/S1070428017080097.
  3. Sakharov P.A., Rostovskii N.V., Khlebnikov A.F., Novikov M.S. “Annulation of five-membered cyclic enols with 3-aryl-2H-azirines: Catalytic versus non-catalytic cycloaddition” Tetrahedron 2017, 73, 4663. DOI: org/10.1016/j.tet.2017.06.037.
  4. Rostovskii N.V., Ruvinskaya J.O., Novikov M.S., Khlebnikov A.F., Smetanin I.A., Agafonova A.V. “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. DOI: 10.1021/acs.joc.6b02389.
  5. Zavyalov K.V., Novikov M.S., Khlebnikov A.F., Rostovskii N.V. “(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.
  6. Smetanin I.A., Novikov M.S., Agafonova A.V., Rostovskii N.V, Khlebnikov A.F., Kudryavtsev I.V., Terpilowski M.A., Serebriakova M.K., Trulioff A.S., Goncharov N.V. “A novel strategy for the synthesis of thermally stable and apoptosis-inducing 2,3-dihydroazetes” Org. Biomol. Chem. 2016, 14, 4479. DOI: 10.1039/c6ob00588h.
  7. Rostovskii N.V., Sakharov P.A., Novikov M.S., Khlebnikov A.F., Starova G.L. “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. DOI:10.1021/acs.orglett.5b01883.
  8. Smetanin I.A., Novikov M.S., Rostovskii N.V., Khlebnikov A.F., Starova G.L., Yufit D.S. “4-Halo-2-azabuta-1,3-dienes as intermediates in the rhodium carbenoid-initiated transformation of 2H-azirines into 2,3-dihydroazetes and 2,5-dihydrooxazoles” Tetrahedron 2015, 71, 4616. DOI:org/10.1016/j.tet.2015.05.022.
  9. Rostovskii N.V., Novikov M.S., Khlebnikov A.F., Starova G.L., Avdontseva M.S. “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. DOI:10.3762/bjoc.11.35.
  10. Novikov M.S., Khlebnikov A.F., Rostovskii N.V., Tcyrulnikov S., Suhanova A.A., Zavyalov K.V., Yufit  D.S. “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. DOI: 10.1021/jo501051n.
  11. Zavyalov K.V., Novikov M.S., Khlebnikov A.F., Pakalnis V.V. “Selective syntheses of 2H-1,3-oxazines and 1H-pyrrol-3(2H)-ones via temperature-dependent Rh(II)-carbenoid-mediated 2H-azirinering expansion” Tetrahedron 2014, 70, 3377. DOI: org/10.1016/j.tet.2014.03.101.
  12. Zavyalov K.V., Novikov M.S., Khlebnikov A.F., Yufit D.S. “Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines“ Tetrahedron 2013, 69, 4546. DOI: org/10.1016/j.tet.2013.04.022.
  13. Rostovskii N.V., Novikov M.S., Khlebnikov A.F., Khlebnikov V.A., Korneev S.M. “Cu(II)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles” Tetrahedron 2013, 69, 4292. DOI: 10.1039/c3ob40708j.
  14. Rostovskii N.V., Novikov M.S., Khlebnikov A. F., Korneev S.M., Yufit D.S. “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. DOI: 10.1039/c3ob40708j.
  15. Novikov M.S., Smetanin I.A., Khlebnikov A.F., Rostovskii N.V., Yufit D.S. “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.
  16. Kobylianskii I.J., Novikov M.S., Khlebnikov A.F. “Formation and reactivity of gem-difluoro-substituted pyridinium ylides: Experimental and DFT investigation” J. Fluorine Chem. 2011, 132, 175. DOI: org/10.1016/j.jfluchem.2010.12.013

Co-authorship in review articles

  1. Khlebnikov A.F., Novikov M.S. “Ring Expansions of Asirines and Azetines” in Topics in Heterocyclic Chemistry: Synthesis of 4- To 7-Membered Heterocycles by Ring Expansion; D’hooghe M., Ha H.-J., Eds.; Springer: Geneva, Switzerland, 2016; Vol. 41, pp 143.
  2. Galenko E.E., Khlebnikov A.F., Novikov M.S. “Isoxazole-azirine isomerization as a reactivity switch in the synthesis of Heterocycles” Chem. Heterocycl. Comp. 2016, 52, 637.
  3. Khlebnikov A.F., Novikov M.S. “Recent advances in 2H-azirine chemistry” Tetrahedron 2013, 69, 3363.
  4. Khlebnikov A.F., Novikov M.S. “Fused aziridines as sources of azomethine ylides” Chem. Heterocycl. Comp. 2012, 48, 179.