J. Org. Chem. 2/2018
Chem. – Eur. J. 4/2016
Chem. – Eur. J. 13/2015
Chem. Commun. 98/2013

Publications

57. O. A. Ivanova, V. V. Shorokhov, I. A. Andreev, N. K. Ratmanova, V. B. Rybakov, E. D. Strel’tsova, I. V. Trushkov. Synthesis of 2-[2-(ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione. Molbank 2023, 2023, M1604. DOI: 10.3390/M1604

56. V. V. Shorokhov, D. S. Lebedev, M. A. Boichenko, S. S. Zhokhov, I. V. Trushkov, O. A. Ivanova. A simple method for the synthesis of isoindoline derivatives. Chem. Heterocycl. Compd. 2023 (Khim. Geterotsikl. Soed. 2023, 59, 54–62). DOI: 10.1007/s10593-023-03162-6

55. T. A. Shestimerova, I. A. Andreev, N. K. Ratmanova, I. V. Trushkov, A. N. Kuznetsov, A. V. Shevelkov. Crystal and electronic structure of thiazolium pentaiodide: an experimental and theoretical study of covalent and non-covalent bonds. Struct. Chem. 2023. DOI: 10.1007/s11224-022-02097-6 (In collaboration with Prof. Shevelkov lab)

54. M. A. Boichenko, A. Yu. Plodukhin, V. V. Shorokhov, D. S. Lebedev, A. V. Filippova, S. S. Zhokhov, E. A. Tarasenko, V. B. Rybakov, I. V. Trushkov, O. A. Ivanova. Synthesis of 1,5-substituted pyrrolidin-2-ones from donor–acceptor cyclopropanes and anilines/benzylamines. Molecules 2022, 27, 8468. DOI: 10.3390/molecules27238468

53. A. E. Vartanova, A. Yu. Plodukhin, M. A. Boichenko, V. V. Shorokhov, S. S. Zhokhov, I. V. Trushkov, O. A. Ivanova. Ring expansion of donor—acceptor cyclopropanes bearing arylcarbamoyl group into 1,5-diarylpyrrolidin-2-ones. Russ. Chem. Bull. 2022, 71, 2431–2440. DOI: 10.1007/s11172-022-3671-3

52. A. E. Vartanova, I. I. Levina, N. K. Ratmanova, I. A. Andreev, O. A. Ivanova, I. V. Trushkov. Ambident reactivity of 5-aminopyrazoles towards donor-acceptor cyclopropanes. Org. Biomol. Chem. 2022, 20, 7795–7802. DOI: 10.1039/D2OB01490D

51. I. A. Andreev, M. A. Boichenko, N. K. Ratmanova, O. A. Ivanova, I. I. Levina, V. N. Khrustalev, I. A. Sedov, I. V. Trushkov. 4-(Dimethylamino)pyridinium azide in protic ionic liquid media as a stable equivalent of hydrazoic acid. Adv. Synth. Catal. 2022, 364, 2403–2415. DOI: 10.1002/adsc.202200486

50. A. A. Fadeev, A. S. Makarov, O. A. Ivanova, M. G. Uchuskin, I. V. Trushkov. Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans. Org. Chem. Front. 2022, 9, 737–744. DOI: 10.1039/D1QO01646F (In collaboration with Perm State University)

49. M. А. Boichenko, K. V. Anisovich, M. S. Shad, S. S. Zhokhov, V. B. Rybakov, W. Dehaen, I. V. Truhskov, O. А. Ivanova. Oxidative cyclization of 5-aryl-1-benzyl-1,2,3-triazoles bearing electron-rich aromatic groups: ortho/ortho and ortho/ipso coupling. Chem. Heterocycl. Compd. 2021, 57, 817–822 (Khim. Geterotsikl. Soed. 2021, 57, 817–822). DOI: 10.1007/s10593-021-02985-5 (In collaboration with Wim Dehaen lab)

48. A. E. Vartanova, A. Yu. Plodukhin, N. K. Ratmanova, I. A. Andreev, M. N. Anisimov, N. B. Gudimchuk, V. B. Rybakov, I. I. Levina, O. A. Ivanova, I. V. Trushkov, I. V. Alabugin. Expanding stereoelectronic limits of endo–tet cyclizations: synthesis of benz[b]azepines from donor–acceptor cyclopropanes. J. Am. Chem. Soc. 2021, 143, 13952–13961. DOI: 10.1021/jacs.1c07088 (In collaboration with Prof. Igor V. Alabugin)

• Highlighted in SYNFACTS as a Synfact of the Month. SYNFACTS 2021, 17, 1317. DOI: 10.1055/s-0041-1737106

47. A. E. Vartanova, I. I. Levina, V. B. Rybakov, O. A. Ivanova, I. V. Trushkov. Donor–acceptor cyclopropane ring opening with 6-amino-1,3-dimethyluracil and its use in pyrimido[4,5-b]azepines synthesis. J. Org. Chem. 2021, 86, 12300–12308. DOI: 10.1021/acs.joc.1c01064

46. A. Jacob, P. Barkawitz, I. A. Andreev, N. K. Ratmanova, I. V. Trushkov, D. B. Werz. Cycloaddition of donor-acceptor cyclopropanes with thiocyanate: a facile and efficient synthesis of 2-amino-4,5-dihydrothiophenes. Synlett 2021, 32, 901–904. DOI: 10.1055/a-1385-2385 (In collaboration with Daniel B. Werz lab)

45. I. A. Andreev, N. K. Ratmanova, A. U. Augustin, O. A. Ivanova, I. I. Levina, V. N. Khrustalev, D. B. Werz, I. V. Trushkov. Protic ionic liquid as reagent, catalyst, and solvent: 1‐methylimidazolium thiocyanate. Angew. Chem. Int. Ed. 2021, 60, 7927–7934. DOI: 10.1002/anie.202016593 (In collaboration with Daniel B. Werz lab)

44. A. A. Fadeev, A. O. Chagarovskiy, A. S. Makarov, I. I. Levina, O. A. Ivanova, M. G. Uchuskin, I. V. Trushkov. Synthesis of (het)aryl 2-(2-hydroxyaryl)cyclopropyl ketones. Molecules 2020, 25, 5748. DOI: 10.3390/molecules25235748 (In collaboration with Perm State University)

43. L. I. Kuznetsova, A. O. Chagarovskiy, I. I. Levina, V. B. Rybakov, O. A. Ivanova, I. V. Trushkov. A simple synthesis of 2-{2-[(arylmethylidene)amino]-indazol-3-yl}malonate esters. Chem. Heterocycl. Compd. 2020, 56, 555–561 (Khim. Geterotsikl. Soed. 2020, 56, 555–561). DOI: 10.1007/s10593-020-02699-0

42. N. K. Ratmanova, I. A. Andreev, A. V. Leontiev, D. Momotova, A. M. Novoselov, O. A. Ivanova, I. V. Trushkov. Strategic approaches to the synthesis of pyrrolizidine and indolizidine alkaloids. Tetrahedron 2020, 76 (14), 131031. DOI: 10.1016/j.tet.2020.131031

• Part of special issue: Tetrahedron Reviews

41. N. K. Ratmanova, I. A. Andreev, I. V. Trushkov. Methods for the synthesis of immunostimulant plerixafor. Chem. Heterocycl. Compd. 2020, 56, 30–35 (Khim. Geterotsikl. Soed. 2020, 56, 30–35). DOI: 10.1007/s10593-020-02617-4

40. H. M. Nguyen, H. R. Chand, N. E. Golantsov, I. V. Trushkov, L. G. Voskressensky. Cyclopentene assembly by microwave-assisted domino reaction of donor–acceptor cyclopropanes with ketals. Synlett 2020, 31, 295–299. DOI: 10.1055/s-0039-1690775 (In collaboration with RUDN University)

39. M. A. Boichenko, A. O. Chagarovskiy, V. B. Rybakov, I. V. Trushkov, O. A. Ivanova. Dimethyl 2-{[2-(2-methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate. Molbank 2020, M1107. DOI: 10.3390/M1107

38. M. A. Boichenko, I. A. Andreev, A. O. Chagarovskiy, I. I. Levina, S. S. Zhokhov, I. V. Trushkov, O. A. Ivanova. Ring opening of donor–acceptor cyclopropanes with cyanide ion and its surrogates. J. Org. Chem. 2020, 85, 1146–1157. DOI: 10.1021/acs.joc.9b03098

37. A. O. Chagarovskiy, V. V. Kuznetsov, O. A. Ivanova, A. S. Goloveshkin, I. I. Levina, N. N. Makhova, I. V. Trushkov. Synthesis of 1-substituted pyrazolines by reaction of donor–acceptor cyclopropanes with 1,5-diazabicyclo[3.1.0]hexanes. Eur. J. Org. Chem. 2019, 2019, 5475–5485. DOI: 10.1002/ejoc.201900579

36. M. A. Boichenko, I. Yu. Babkin, S. G. Kobylskoy, A. O. Chagarovskiy, O. A. Ivanova, I. V. Trushkov. 4b,5,6,9-Tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin-7-one. Molbank 2019, 2019, M1061. DOI: 10.3390/M1061

35. A. O. Chagarovskiy, E. D. Strel’tsova, V. B. Rybakov, I. I. Levina, I. V. Trushkov. Synthesis of 2,3-diaryl-2,3,4,4а-tetrahydro-5Н-indeno[1,2-c]pyridazin-5-ones. Chem. Heterocycl. Compd. 2019, 55, 240–245 (Khim. Geterotsikl. Soed. 2019, 55, 240–245). DOI: 10.1007/s10593-019-02448-y

34. O. A. Ivanova, I. V. Trushkov. Donor–acceptor cyclopropanes in the synthesis of carbocycles. Chem. Rec. 2019, 19, 2189–2208. DOI: 10.1002/tcr.201800166

33. O. A. Ivanova, V. A. Andronov, I. I. Levina, A. O. Chagarovskiy, L. G. Voskressensky, I. V. Trushkov. Convenient Synthesis of Functionalized Cyclopropa[c]coumarin-1a-carboxylates. Molecules 2019, 24, 57. DOI: 10.3390/molecules24010057

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32. O. A. Ivanova, V. A. Andronov, V. S. Vasin, A. N. Shumsky, V. B. Rybakov, L. G. Voskressensky, I. V. Trushkov. Expanding the reactivity of donor–acceptor cyclopropanes: synthesis of benzannulated five-membered heterocycles via intramolecular attack of a pendant nucleophilic group. Org. Lett. 2018, 20, 7947–7952. DOI: 10.1021/acs.orglett.8b03491

• Featured in the Virtual Issue “From Russia, With Chemistry”, ACS core organic journals 2020

ol-2018-034915_0008

31. M. A. Boichenko, O. A. Ivanova, I. A. Andreev, A. O. Chagarovskiy, I. I. Levina, V. B. Rybakov, D. A. Skvortsov, I. V. Trushkov. Convenient approach to polyoxygenated dibenzo[c,e]pyrrolo[1,2-a]azepines from donor–acceptor cyclopropanes. Org. Chem. Front. 2018, 5, 2829–2834. DOI: 10.1039/C8QO00742J

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30. A. O. Chagarovskiy, V. S. Vasin, V. V. Kuznetsov, O. A. Ivanova, V. B. Rybakov, A. N. Shumsky, N. N. Makhova, I. V. Trushkov. (3+3)-Annulation of donor–acceptor cyclopropanes with diaziridines. Angew. Chem. Int. Ed. 2018, 57, 10338–10342. DOI: 10.1002/anie.201805258

anie201805258-toc-0001-m

29. O. A. Ivanova, A. O. Chagarovskiy, A. N. Shumsky, V. D. Krasnobrov, I. I. Levina, I. V. Trushkov. Lewis acid triggered vinylcyclopropane-cyclopentene rearrangement. J. Org. Chem. 2018, 83, 543–560. DOI: 10.1021/acs.joc.7b02351

• Featured in the Virtual Issue “From Russia, With Chemistry”, ACS core organic journals 2020

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28. Y. V. Tomilov, L. G. Menchikov, R. A. Novikov, O. A. Ivanova, I. V. Trushkov. Methods for the synthesis of donor-acceptor cyclopropanes. Russ. Chem. Rev. 2018, 87, 201–250. (Usp. Khim. 2018, 87, 201–250). DOI: 10.1070/RCR4787

98ZDuLQKu0M

27. A. O. Chagarovskiy, O. A. Ivanova, A. N. Shumsky, I. V. Trushkov. Synthesis of hexahydropyridazin-3-ones by reactions between donor-acceptor cyclopropanes and phenylhydrazine. Chem. Heterocycl. Compd. 2017, 53, 1220–1227 (Khim. Geterotsikl. Soed. 2017, 53, 1220–1227). DOI: 10.1007/s10593-018-2203-4

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26. A. S. Pavlova, O. A. Ivanova, A. O. Chagarovskiy, N. S. Stebunov, N. V. Orlov, A. N. Shumsky, E. M. Budynina, V. B. Rybakov, I. V. Trushkov. Domino Staudinger/aza-Wittig/Mannich reaction: an approach to diversity of di- and tetrahydropyrrole scaffolds. Chem. – Eur. J. 2016, 22, 17967–17971. DOI: 10.1002/chem.201604056

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25. E. M. Budynina, K. L. Ivanov, A. O. Chagarovskiy, V. B. Rybakov, I. V. Trushkov, M. Y. Melnikov. From umpolung to alternation: modified reactivity of donor–acceptor cyclopropanes towards nucleophiles in reaction with nitroalkanes. Chem. – Eur. J. 2016, 22, 3692–3696. DOI: 10.1002/chem.201504593

25

24. O. A. Ivanova, E. M. Budynina, V. N. Khrustalev, D. A. Skvortsov, I. V. Trushkov, M. Y. Melnikov. A straightforward approach to tetrahydroindolo[3,2-b]carbazoles and 1-indolyltetrahydrocarbazoles via [3+3] cyclodimerization of indole-derived cyclopropanes. Chem. – Eur. J. 2016, 22, 1223–1227. DOI: 10.1002/chem.201502287

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23. A. O. Chagarovskiy, E. M. Budynina, O. A. Ivanova, V. B. Rybakov, I. V. Trushkov, M. Y. Melnikov. Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure–ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine. Org. Biomol. Chem. 2016, 14, 2905–2915. DOI: 10.1039/C5OB02596F

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22. E. V. Villemson, E.M. Budynina, O. A. Ivanova, D. A. Skvortsov, I. V. Trushkov, M. Y. Melnikov. Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes. RSC Adv. 2016, 6, 62014–62018. DOI: 10.1039/c6ra11233a

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21. I. V. Trushkov. Indole-derived donor-acceptor cyclopropanes. Isr. J. Chem. 2016, 56, 369–384. DOI: 10.1002/ijch.201500069

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20. E. R. Rakhmankulov, K. L. Ivanov, E. M. Budynina, O. A. Ivanova, A. O. Chagarovskiy, D. A. Skvortsov, G. V. Latyshev, I. V. Trushkov, M. Y. Melnikov. Lewis and Brӧnsted acid induced (3+2)-annulation of donor–acceptor cyclopropanes to alkynes: indene assembly. Org. Lett. 2015, 17, 770–773. DOI: 10.1021/ol5037562

20

19. K. L. Ivanov, E. V. Villemson, E. M. Budynina, O. A. Ivanova, I. V. Trushkov, M. Y. Melnikov. Ring opening of donor–acceptor cyclopropanes with the azide ion: a tool for construction of N-heterocycles. Chem. – Eur. J. 2015, 21, 4975–4987. DOI: 10.1002/chem.201405551

19

18. E. M. Budynina, O. A. Ivanova, A. O. Chagarovskiy, Y. K. Grishin, I. V. Trushkov, M. Y. Melnikov. Formal [3+2]-cycloaddition of donor–acceptor cyclopropanes to 1,3-dienes: cyclopentane assembly. J. Org. Chem. 2015, 80, 12212–12223. DOI: 10.1021/acs.joc.5b02146

18

17. O. A. Ivanova, E. M. Budynina, V. N. Khrustalev, I. V. Trushkov, M. Y. Melnikov. New domino dimerization of cyclopropylindoles: synthesis of 1,3-bis(indolyl)cyclopentanes. Chem. Heterocycl. Compd. 2015, 51, 936–939 (Khim. Geterotsikl. Soed. 2015, 51, 936–939). DOI: 10.1007/s10593-015-1798-y

17

16. A. O. Chagarovskiy, E. M. Budynina, O. A. Ivanova, E. V. Villemson, V. B. Rybakov, I. V. Trushkov, M. Y. Melnikov. Reaction of Corey ylide with α,β-unsaturated ketones: tuning of chemoselectivity toward dihydrofuran synthesis. Org. Lett. 2014, 16, 2830–2833. DOI: 10.1021/ol500877c

16

15. O. A. Ivanova, E. M. Budynina, D. A. Skvortsov, I. V. Trushkov, M. Y. Melnikov. Shortcut approach to cyclopenta[b]indoles by [3+2]-cyclodimerization of indole-derived cyclopropanes. Synlett 2014, 25, 2289–2292. DOI: 10.1055/s-0034-1378372

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14. O. A. Ivanova, E. M. Budynina, D. A. Skvortsov, M. Limoge, A. V. Bakin, A. O. Chagarovskiy, I. V. Trushkov, M. Y. Melnikov. A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor–acceptor cyclopropanes. Chem. Commun. 2013, 49, 11482–11484. DOI: 10.1039/C3CC44475A

14

13. Y. A. Volkova, E. M. Budynina, A. E. Kaplun, O. A. Ivanova, A. O. Chagarovskiy, D. A. Skvortsov, V. B. Rybakov, I. V. Trushkov, M. Y. Melnikov. Duality of donor–acceptor cyclopropane reactivity as a three-carbon component in five-membered ring construction: [3+2] annulation versus [3+2] cycloaddition. Chem. – Eur. J. 2013, 19, 6586–6590. DOI: 10.1002/chem.201300731

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12. A. O. Chagarovskiy, O. A. Ivanova, E. M. Budynina, E. L. Kolychev, M. S. Nechaev, I. V. Trushkov, M. Y. Melnikov. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway. Russ. Chem. Bull. 2013, 62, 2407–2423 (Izv. Akad. Nauk. Ser. Khim. 2013, 2407–2423). DOI: 10.1007/s11172-013-0349-x

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11. A. O. Chagarovskiy, K. L. Ivanov, E. M. Budynina, O. A. Ivanova, I. V. Trushkov. Reaction of dimethyl (S)-2-(p-tolyl)cyclopropane-1,1-dicarboxylate with acetonitrile. Chem. Heterocycl. Compd. 2012, 48, 825–827 (Khim. Geterotsikl. Soed. 2012, 886–888). DOI: 10.1007/s10593-012-1062-7

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10. O. A. Ivanova, E. M. Budynina, A. O. Chagarovskiy, A. E. Kaplun, I. V. Trushkov, M. Y. Melnikov. Lewis acid-catalyzed [3+4] annulation of 2-(heteroaryl)cyclopropanes-1,1-dicarboxylates with cyclopentadiene. Adv. Synth. Catal. 2011, 353, 1125–1134. DOI: 10.1002/adsc.201000783

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9. O. A. Ivanova, E. M. Budynina, A. O. Chagarovskiy, E. R. Rakhmankulov, I. V. Trushkov, A. V. Semeykin, N. L. Shimanovskii, M. Y. Melnikov. Domino cyclodimerization of indole-derived donor–acceptor cyclopropanes: one-step construction of pentaleno[1,6-a,b]indole skeleton. Chem. – Eur. J. 2011, 17, 11738–11742. DOI: 10.1002/chem.201101687

9

8. O. A. Ivanova, E. M. Budynina, A. O. Chagarovskiy, I. V. Trushkov, M. Y. Melnikov. (3+3)-Cyclodimerization of donor–acceptor cyclopropanes. Three routes to six-membered rings. J. Org. Chem. 2011, 76, 8852–8868. DOI: 10.1021/jo201612w

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7. A. O. Chagarovskiy, O. A. Ivanova, E. M. Budynina, I. V. Trushkov, M. Y. Melnikov. (3+2) Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung. Tetrahedron Lett. 2011, 52, 4421–4425. DOI: 10.1016/j.tetlet.2011.06.059

7

6. M. Y. Melnikov, E. M. Budynina, O. A. Ivanova, I. V. Trushkov. Recent advances in ring-forming reactions of donor–acceptor cyclopropanes. Mendeleev Commun. 2011, 21, 293–301. DOI: 10.1016/j.mencom.2011.11.001

5. A. O. Chagarovskiy, O. A. Ivanova, E. R. Rakhmankulov, E. M. Budynina, I. V. Trushkov, M. Y. Melnikov. Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1-dicarboxylates: a new efficient route to 2-styrylmalonates. Adv. Synth. Catal. 2010, 352, 3179–3184. DOI: 10.1002/adsc.201000636

5

4. A. O. Chagarovskiy, E. M. Budynina, O. A. Ivanova, I. V. Trushkov. First synthesis of 2-alkyl-5-aryl-3,3-bis(methoxycarbonyl)-4,5-dihydropyrroles. Chem. Heterocycl. Compd. 2010, 46, 120–122 (Khim. Geterotsikl. Soed. 2010, 139-141). DOI: 10.1007/s10593-010-0478-1

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3. A. O. Chagarovskiy, E. M. Budynina, O. A. Ivanova, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii. Lewis acid-catalyzed reactions of donor–acceptor cyclopropanes with furan derivatives. Tetrahedron 2009, 65, 5385–5392. DOI: 10.1016/j.tet.2009.04.061

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2. O. A. Ivanova, E. M. Budynina, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii. Lewis acid catalyzed reactions of donor–acceptor cyclopropanes with anthracenes. Eur. J. Org. Chem. 2008, 5329–5335. DOI: 10.1002/ejoc.200800620

2

1. O. A. Ivanova, E. M. Budynina, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii. Donor–acceptor cyclopropanes as three-carbon components in a [4+3] cycloaddition reaction with 1,3-diphenylisobenzofuran. Angew. Chem. Int. Ed. 2008, 47, 1107–1110 (Angewandte Chemie 2008, 120, 1123–1126). DOI: 10.1002/anie.200704438

1

Publications (in collaboration with Perm State University)

39. P. N. Chalikidi, T. T. Magkoev, A. V. Gutnov, O. P. Demidov, M. G. Uchuskin, I. V. Trushkov, V. T. Abaev. One-step synthesis of triphenylphosphonium salts from (het)arylmethyl alcohols. J. Org. Chem. 2021, 86, 9838–9846. DOI: 10.1021/acs.joc.1c00733

38. R. O. Shcherbakov, D. A. Eshmemet’eva, A. A. Merkushev, I. V. Trushkov, M. G. Uchuskin. Transformation of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones to prop-2-en-1-ones via oxidative furan dearomatization/2-ene-1,4,7-triones cyclization. Molecules 2021, 26, 2637. DOI: 10.3390/molecules26092637

37. A. A. Merkushev, A. S. Makarov, P. M. Shpuntov, V. T. Abaev, I. V. Trushkov, M. G. Uchuskin. Oxidative rearrangement of 2‐(2‐aminobenzyl)furans: synthesis of functionalized indoles and carbazoles. Eur. J. Org. Chem. 2021, 1274–1285. DOI: 10.1002/ejoc.202001608

36. E. Y. Zelina, T. A. Nevolina, L. N. Sorotskaja, D. A. Skvortsov, I. V. Trushkov, M. G. Uchuskin. Route to pyrrolo[1,2-a]quinoxalines via a furan ring opening-pyrrole ring closure sequence. Tetrahedron Lett. 2020, 61 (9), 151532. DOI: 10.1016/j.tetlet.2019.151532

35. E. Y. Zelina, T. A. Nevolina, D. A. Skvortsov, I. V. Trushkov, M. G. Uchuskin. A route to (het)arene-annulated pyrrolo[1,2-d][1,4]diazepines via the expanded intramolecular Paal–Knorr reaction: nitro group and furan ring as equivalents of amino group and 1,4-diketone. J. Org. Chem. 2019, 84, 13707–13720. DOI: 10.1021/acs.joc.9b01925

34. A. S. Makarov, A. E. Kekhvaeva, P. N. Chalikidi, V. T. Abaev, I. V. Trushkov, M. G. Uchuskin. A simple synthesis of densely substituted benzofurans by domino reaction of 2-hydroxybenzyl alcohols with 2-substituted furans. Synthesis 2019, 51, 3747–3757. DOI: 10.1055/s-0039-1690000

33. А. А. Меrkushev, I. V. Тrushkov, М. G. Uchuskin. Modern methods for the synthesis of δ-carbolines. Russ. Chem. Bull. 2019, 68, 681–690 (Izv. Akad. Nauk. Ser. Khim. 2019, 681–690). DOI: 10.1007/s11172-019-2475-6

32. I. V. Trushkov, M. G. Uchuskin, V. T. Abaev, O. V. Serdyuk. Indolylvinyl ketones: building blocks for the synthesis of natural products and bioactive compounds. Synthesis 2019, 51, 787–815. DOI: 10.1055/s-0037-1611702

31. Y. Zelina, T. A. Nevolina, L. N. Sorotskaja, D. A. Skvortsov, I. V. Trushkov, M. G. Uchuskin. A general synthetic route to isomeric pyrrolo[1,2-x][1,4]diazepinones. J. Org. Chem. 2018, 83, 11747–11757. DOI: 10.1021/acs.joc.8b01669

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30. A. S. Makarov, M. G. Uchuskin, I. V. Trushkov. Furan oxidation reactions in the total synthesis of natural products. Synthesis 2018, 50, 3059–3086. DOI: 10.1055/s-0037-1610021

i_z0118_ga_10-1055_s-0037-1610021

29. P. N. Chalikidi, M. G. Uchuskin, I. V. Trushkov, V. T. Abaev, O. V. Serdyuk. Facile synthesis of β-keto sulfones employing Fenton’s reagent in DMSO. Synlett 2018, 29, 571–575. DOI: 10.1055/s-0036-1589151

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28. A. S. Makarov, A. E. Kekhvaeva, C. J. J. Hall, D. R. Price, I. V. Trushkov, M. G. Uchuskin. CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step. Tetrahedron 2017, 73, 7042–7053. DOI: 10.1016/j.tet.2017.10.054

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27. A. A. Merkushev, V. N. Strel’nikov, M. G. Uchuskin, I. V. Trushkov. A simple synthesis of benzofurans by acid-catalyzed domino reaction of salicyl alcohols with N-tosylfurfurylamine. Tetrahedron 2017, 73, 6523–6529. DOI: 10.1016/j.tet.2017.09.043

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26. A. A. Fadeev, M. G. Uchuskin, I. V. Trushkov, A. S. Makarov. Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds. Chem. Heterocycl. Compd. 2017, 53, 1286–1293 (Khim. Geterotsikl. Soed. 2017, 53, 1286–1293). DOI: 10.1007/s10593-018-2206-1

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25. A. S. Makarov, A. A. Merkushev, M. G. Uchuskin, I. V. Trushkov. Oxidative Furan-to-indole rearrangement. Synthesis of 2-(2-acylvinyl)indoles and flinderole C analogues. Org. Lett. 2016, 18, 2192–2195. DOI: 10.1021/acs.orglett.6b00805

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24. A. S. Makarov, L. N. Sorotskaja, M. G. Uchuskin, I. V. Trushkov. Synthesis of quinolines via acid-catalyzed cyclodehydration of 2-(tosylamino)chalcones. Chem. Heterocycl. Compd. 2016, 52, 1087–1091 (Khim. Geterotsikl. Soed. 2016, 52, 1087–1091). DOI: 10.1007/s10593-017-2010-3

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23. V. T. Abaev, I. V. Trushkov, M. G. Uchuskin. The Butin reaction. Chem. Heterocycl. Compd. 2016, 52, 973–995 (Khim. Geterotsikl. Soed. 2016, 52, 973–995). DOI: 10.1007/s10593-017-1996-x

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22. I. V. Trushkov, M. G. Uchuskin, A. V. Butin. Furan’s gambit: electrophile-attack-triggered sacrifice of furan rings for the intramolecular construction of azaheterocycles. Eur. J. Org. Chem. 2015, 2999–3016. DOI: 10.1002/ejoc.201403580

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21. A. S. Pilipenko, M. G. Uchuskin, I. V. Trushkov, A. V. Butin. A Simple route to γ-carbolines and indolizino[7,6-b]indoles. Tetrahedron 2015, 71, 8786–8790. DOI: 10.1016/j.tet.2015.09.046

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20. V. T. Abaev, A. T. Plieva, P. N. Chalikidi, M. G. Uchuskin, I. V. Trushkov, A. V. Butin. A simple route to polysubstituted indoles exploiting azide induced furan ring opening. Org. Lett. 2014, 16, 4150–4153. DOI: 10.1021/ol5018504

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19. M. G. Uchuskin, N. V. Molodtsova, S. A. Lysenko, V. N. Strel’nikov, I. V. Trushkov, A. V. Butin. Synthesis of indoles by domino reaction of 2-(tosylamino)benzyl alcohols with furfurylamines: two opposite reactivity modes of the α-carbon of the furan ring in one process. Eur. J. Org. Chem. 2014, 2508–2515. DOI: 10.1002/ejoc.201301762

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18. A. V. Butin, I. V. Trushkov, O. V. Serdyuk, V. T. Abaev. Fluorinated furans and benzofurans in Fluorine in Heterocyclic Chemistry (ed. by V. Nenajdenko) Springer, Heidelberg, 2014, Vol. 1: 5-Membered Heterocycles and Macrocycles, 181–231. DOI: 10.1007/978-3-319-04346-3_5

17. I. V. Trushkov, T. A. Nevolina, V. A. Shcherbinin, L. N. Sorotskaya, A. V. Butin. Furan ring opening–pyrrole ring closure. A simple route to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-3-ones. Tetrahedron Lett. 2013, 54, 3974–3976. DOI: 10.1016/j.tetlet.2013.05.066

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16. A. V. Fin’ko, V. O. Babikov, A. S. Pilipenko, V. T. Abaev, I. V. Trushkov, A. V. Butin. Acid-catalyzed cascade rearrangement of 4-acetoxy-9-furylnaphtho[2,3-b]furans. Monatsh. Chem. 2013, 144, 1711–1723. DOI: 10.1007/s00706-013-1075-7

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15. M. G. Uchuskin, A. S. Pilipenko, O. V. Serdyuk, I. V. Trushkov, A. V. Butin. From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives. Org. Biomol. Chem. 2012, 10, 7262–7265. DOI: 10.1039/C2OB25836F

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14. M. G. Uchuskin, N. V. Molodtsova, V. T. Abaev, I. V. Trushkov, A. V. Butin. Furan ring opening–indole ring closure: SnCl2-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles. Tetrahedron 2012, 68, 4252–4258. DOI: 10.1016/j.tet.2012.03.069

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13. A. S. Pilipenko, V. M. Mel’chin, I. V. Trushkov, D. A. Cheshkov, A. V. Butin. Furan ring opening–indole ring closure: recyclization of 2-(2-aminophenyl)furans into 2-(2-oxoalkyl)indoles. Tetrahedron 2012, 68, 619–627. DOI: 10.1016/j.tet.2011.10.114

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12. A. V. Butin, F. A. Tsiunchik, O. N. Kostyukova, M. G. Uchuskin, I. V. Trushkov. Furan ring opening – pyridine ring closure: new route to quinolines under the Bischler-Napieralski reaction conditions. Synthesis 2011, 2629–2638. DOI: 10.1055/s-0030-1260118

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11. A. V. Butin, M. G. Uchuskin, A. S. Pilipenko, O. V. Serdyuk, I. V. Trushkov. Unusual reactivity of β-(3-indolyl)-α,β-unsaturated ketones. 2-Acylvinyl group removal by phenylhydrazine hydrochloride. Tetrahedron Lett. 2011, 52, 5255–5258. DOI: 10.1016/j.tetlet.2011.07.136

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10. A. V. Butin, O. N. Kostyukova, F. A. Tsiunchik, M. G. Uchuskin, O. V. Serdyuk, I. V. Trushkov. Synthesis of tetracyclic system of 2,4-di(tert-Butyl)-6,7-dihydrofuro[2′,3′:3,4]cyclohepta[1,2-b]indole. J. Heterocycl. Chem. 2011, 48, 684–690. DOI: 10.1002/jhet.635

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9. A. V. Butin, F. A. Tsiunchik, N. O. Kostyukova, I. V. Trushkov. Novel route to quinolines via recyclization of furans. Chem. Heterocycl. Compd. 2011, 46, 1539–1541 (Khim. Geterotsikl. Soed. 2010, 1900–1903). DOI: 10.1007/s10593-011-0707-2

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8. A. V. Butin, T. A. Nevolina, V. A. Shcherbinin, I. V. Trushkov, D. A. Cheshkov,  G. D. Krapivin. Furan ring opening–pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines. Org. Biomol. Chem. 2010, 8, 3316–3327. DOI: 10.1039/C002994G

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7. A. V. Butin, M. G. Uchuskin, A. S. Pilipenko, F. A. Tsiunchik, D. A. Cheshkov, I. V. Trushkov. Furan ring-opening/indole ring-closure: Pictet-Spengler-like reaction of 2-(o-aminophenyl)furans with aldehydes. Eur. J. Org. Chem. 2010, 920–926. DOI: 10.1002/ejoc.200901241

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6. A. V. Butin, T. A. Nevolina, V. A. Shcherbinin, M. G. Uchuskin, O. V. Serdyuk, I. V. Trushkov. Furan ring opening–pyrrole ring closure: simple route to 5-alkyl-2-(aminomethyl)pyrroles. Synthesis 2010, 2969–2978. DOI: 10.1055/s-0030-1258165

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5. A. V. Butin, N. O. Kostyukova, F. A. Tsiunchik, S. A. Lysenko, I. V. Trushkov. First example of a synthesis of the tetracyclic 2,4-di(tert-Butyl)-6,7-dihydrofuro[2′,3′:3,4]cyclohepta[1,2-b]indole system. Chem. Heterocycl. Compd. 2010, 46, 117–119 (Khim. Geterotsikl. Soed. 2010, 137–139). DOI: 10.1007/s10593-010-0477-2

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4. A. V. Butin, S. K. Smirnov, F. A. Tsiunchik, M. G. Uchushkin, I. V. Trushkov. Recyclization of (2-aminophenyl)bis(5-tert-butyl-2-furyl)methanes into indole derivatives: unusual dependence on substituent at nitrogen atom. Synthesis 2008, 2943–2952. DOI: 10.1055/s-2008-1067248

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3. A. V. Butin, S. K. Smirnov, I. V. Trushkov. The effect of N-substituent on recyclization of (2-aminoaryl)bis(5-tert-butyl-2-furyl)methanes: synthesis of 3-furylindoles and triketoindoles. Tetrahedron Lett. 2008, 49, 20–24. DOI: 10.1016/j.tetlet.2007.11.015

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2. A. V. Butin, A. S. Dmitriev, M. G. Uchushkin, V. T. Abaev, I. V. Trushkov. Simple and convenient synthesis of 4-unsubstituted-3-(3-oxoalkyl)isocoumarins. Synth. Commun. 2008, 38, 1569–1578. DOI: 10.1080/00397910801929382

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1. A. V. Butin, A. S. Dmitriev, O. N. Kostyukova, V. T. Abaev, I. V. Trushkov. Synthesis of the 4,10-dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one system by a furan recyclization reaction. Synthesis 2007, 2208–2214. DOI: 10.1055/s-2007-983764

Other publications

18. I. V. Veselov, I. V. Trushkov, N. S. Zefirov, G. V. Grishina. trans-4-Amino-3-hydroxypiperidines. Regio- and stereoselective synthesis. Russ. J. Org. Chem. 2009, 45, 1050–1060 (Zh. Org. Khim. 2009, 45, 1062–1072). DOI: 10.1134/S1070428009070124

17. I. V. Trushkov, M. M. Silaev, N. D. Chuvylkin. Acyclic and cyclic forms of the radicals HO4·, CH3O4·, and C2H5O4·: ab initio quantum chemical calculations. Russ. Chem. Bull. 2009, 58, 489–492 (Izv. Akad. Nauk. Ser. Khim. 2009, 479–482). DOI: 10.1007/s11172-009-0044-0

16. G. V. Grishina, I. V. Veselov, D. N. Nosik, I. V. Trushkov. Directed synthesis of nanostructures containing two pharmacophore fragments – highly functionalized derivatives of fullerene and piperidine. J. New Medical Technol. 2009, 16, 275–277 (Vest. Novykh Med. Tekhnol. 2009, 16, 275–277).

15. A. A. Goryunkov, N. S. Ovchinnikova, I. V. Trushkov, M. A. Yurovskaya. Synthesis, structures and reactivity of polyhalo[60]fullerenes. Russ. Chem. Rev. 2007, 76, 289–312. (Usp. Khimii, 2007, 76, 323–347). DOI: 10.1070/RC2007v076n04ABEH003668

14. G. V. Gavrilova, I. N. Rusetskaya, A. A. Gavrilov, I. V. Trushkov, D. P. Krut’ko. Bromination of 4-dichloromethyl-4-methylcyclohexa-2,5-dien-1-ones. Synth. Commun. 2007, 37, 2729–2736. DOI: 10.1080/00397910701465958

13. L. N. Sidorov, M. A. Yurovskaya, A. Y. Borshchevskiy, I. V. Trushkov, I. N. Ioffe. Fullerenes. M.: Examen, 2005, 688 pp. (in Russian).

12. I. V. Trushkov, V. K. Brel. Unusual reactivity of 3-chloro-1-pentafluorosulfanylpropene in nucleophilic substitution reactions. Tetrahedron Lett. 2005, 46, 4777–4779. DOI: 10.1016/j.tetlet.2005.05.041

11. S. S. Mochalov, R. A. Gazzaeva, A. N. Fedotov, E. V. Trofimova, I. V. Trushkov, N. S. Zefirov. Cyclopropyl- and allyl-substituted arenes in reaction with dinitrogen tetroxide. Effect of substrate oxidation potential on reaction direction. Russ. J. Org. Chem. 2004, 40, 1098–1112 (Zh. Org. Khim. 2004, 40, 1146–1160). DOI: 10.1023/B:RUJO.0000045888.43245.d7

10. S. S. Kim, I. V. Trushkov, S. K. Sar. Oxidation of alcohols with periodic acid catalyzed by Fe(III)/2-picolinic acid. Bull. Korean Chem. Soc. 2002, 23, 1331–1332. DOI: 10.5012/bkcs.2002.23.9.1331

9. M. A. Yurovskaya, I. V. Trushkov. Cycloaddition to buckminsterfullerene C60: advancements and future prospects. Russ. Chem. Bull. 2002, 51, 367–443 (Izv. Akad. Nauk. Ser. Khim. 2002, 343–413). DOI: 10.1023/A:1015565600068

8. S. A. Yamashkin, I. V. Trushkov, O. B. Tomilin, I. I. Terekhin, M. A. Yurovskaya. Reactivities of 5-, 6- and 7-(enamino)indoles in the synthesis of pyrroloquinolines. Chem. Heterocycl. Compd. 1998, 34, 1050–1065 (Khim. Geterotsikl. Soed. 1998, 1223–1242). DOI: 10.1007/BF02251551

7. I. V. Trushkov, A. V. Karchava, M. A. Yurovskaya. Stereoselectivity in the reduction of chiral indoles to indolines. Chem. Heterocycl. Compd. 1996, 32, 1027–1034 (Khim. Geterotsikl. Soed. 1996, 1199–1208). DOI: 10.1007/BF01164707

6. I. V. Trushkov, E. L. Gaidarova, G. V. Grishina. Quantum-chemical analysis of the conformational and daistereomeric composition of 1,3-dimethyl-4-(S-phenylethylimino)piperidine. Chem. Heterocycl. Compd. 1996, 32, 308–309 (Khim. Geterotsikl. Soed. 1996, 359–360). DOI: 10.1007/BF01169247

5. I. V. Trushkov, N. D. Chuvylkin, A. S. Koz’min, N. S. Zefirov. Correlation methods for analyzing and predicting reactivities in nucleophilic substitution processes. Russ. Chem. Bull. 1995, 44, 777–800 (Izv. Akad. Nauk. Ser. Khim. 1995, 804–826). DOI: 10.1007/BF00696905

4. I. V. Trushkov. Multi-dimensional reaction coordinate diagrams as a method for analysis and prediction of organic reactivity. Mendeleev Chem. J. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva) 1994, 38, № 6, 45–53.

3. I. V. Trushkov, V. M. Promyslov, N. D. Chuvylkin, A. S. Koz’min, N. S. Zefirov. Analysis of organic reactions on the framework of a three dimensional reaction diagram. 2. The estimation of the formation energy of the ion-molecule complexes in the gas-phase SN2 reactions. New J. Chem. 1993, 17, 173–180.

2. I. V. Trushkov, N. D. Chuvylkin, A. S. Koz’min, N. S. Zefirov. Analysis of organic reactions on the framework of a three dimensional reaction diagram. 1. Cubic diagram and its application to nucleophilic substitution reactions. New J. Chem. 1993, 17, 161–171.

1. I. V. Trushkov, V. V. Zhdankin, A. S. Koz’min, N. S. Zefirov. Cubic reaction coordinate diagram in the nucleophilic substitution process. Tetrahedron Lett. 1990, 31, 3199–3200. DOI: 10.1016/S0040-4039(00)94731-2