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RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Divergent approach to 5-cyanotriazoles and triazolo[1,5-a]quinolines based on Pd-catalyzed cyanation of 2-(5-iodotriazolyl)phenylacetic acid derivatives

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PII
S3034630425070191-1
DOI
10.7868/S3034630425070191
Publication type
Article
Status
Published
Authors
R.N. Galashev
  • Affiliation: M.V. Lomonosov Moscow State University, Chemistry Department
G.V. Latyshev
  • Affiliation: M.V. Lomonosov Moscow State University, Chemistry Department
Y.N. Kotovshchikov
  • Affiliation: M.V. Lomonosov Moscow State University, Chemistry Department
N.V. Lukashev
  • Affiliation: M.V. Lomonosov Moscow State University, Chemistry Department
I.P. Beletskaya
  • Affiliation: M.V. Lomonosov Moscow State University, Chemistry Department
Volume/ Edition
Volume 61 / Issue number 7
Pages
983-990
Abstract
Divergent approach to 5-cyanotriazoles and triazolo[1,5-a]quinolines based on Pd-catalyzed cyanation of 2-(5-iodotriazolyl)phenylacetic acid derivatives has been developed. Chemoselectivity is controlled by the choice of a cyanide source. Thus, CuCN leads only to replacement of iodine by nitrile moiety, while KCN induces further cyclization of the cyanation product via intramolecular condensation. The method is applicable to the preparation of both types of heterocyclic compounds in good yields (63—88%).
Keywords
палладиевый катализ цианирование нитрилы гетероциклы триазолы хинолины дивергентный синтез
Date of publication
10.03.2026
Year of publication
2026
Number of purchasers
0
Views
14

References

  1. 1. Scattergood P.A., Sinopoli A., Elliott P.I.P. Coord. Chem. Rev. 2017, 350, 136–154. https://doi.org/10.1016/j.ccr.2017.06.017
  2. 2. Schulze B., Schubert U.S. Chem. Soc. Rev. 2014, 43, 2522–2571. https://doi.org/10.1039/c3cs60386e
  3. 3. Huang D., Zhao P., Astruc D. Coord. Chem. Rev. 2014, 272, 145–165. https://doi.org/10.1016/j.ccr.2014.04.006
  4. 4. Huo J., Hu H., Zhang M., Hu X., Chen M., Chen D., Liu J., Xiao G., Wang Y., Wen Z. RSC Adv. 2017, 7, 2281–2287. https://doi.org/10.1039/c6ra27012c
  5. 5. Kantheti S., Narayan R., Raju K.V.S.N. RSC Adv. 2015, 5, 3687–3708. https://doi.org/10.1039/c4ra12739k
  6. 6. Ben Nejma A., Znati M., Daich A., Othman M., Lawson A.M., Ben Jannet H. Steroids. 2018, 138, 102–107. https://doi.org/10.1016/j.steroids.2018.07.004
  7. 7. Aher N.G., Pore V.S., Mishra N.N., Kumar A., Shukla P.K., Sharma A., Bhat M.K. Bioorg. Med. Chem. Lett. 2009, 19, 759–763. https://doi.org/10.1016/j.bmcl.2008.12.026
  8. 8. Thirumurugan P., Matosiuk D., Jozwiak K. Chem. Rev. 2013, 113, 4905–4979. https://doi.org/10.1021/cr200409f
  9. 9. Agalave S.G., Maujan S.R., Pore V.S. Chem. – Asian J. 2011, 6, 2696–2718. https://doi.org/10.1002/asia.201100432
  10. 10. Rani A., Singh G., Singh A., Maqbool U., Kaur G., Singh J. RSC Adv. 2020, 10, 5610–5635. https://doi.org/10.1039/c9ra09510a
  11. 11. Dheer D., Singh V., Shankar R. Bioorg. Chem. 2017, 71, 30–54. https://doi.org/10.1016/j.bioorg.2017.01.010
  12. 12. Ameziane El Hassani I., Rouzi K., Ameziane El Hassani A., Karrouchi K., Ansar M. Organics. 2024, 5, 450–471. https://doi.org/10.3390/org5040024
  13. 13. Vala D.P., Vala R.M., Patel H.M. ACS Omega. 2022, 7, 36945–36987. https://doi.org/10.1021/acsomega.2c04883
  14. 14. Hein J.E., Fokin V.V. Chem. Soc. Rev. 2010, 39, 1302–1315. https://doi.org/10.1039/b904091a
  15. 15. Haldón E., Nicasio M.C., Pérez P.J. Org. Biomol. Chem. 2015, 13, 9528–9550. https://doi.org/10.1039/C5OB01457C
  16. 16. Neumann S., Biewend M., Rana S., Binder W.H. Macromol. Rapid Commun. 2020, 41, 1900359. https://doi.org/10.1002/marc.201900359
  17. 17. Hein J.E., Tripp J.C., Krasnova L.B., Sharpless K.B., Fokin V.V. Angew. Chem. Int. Ed. 2009, 48, 8018–8021. https://doi.org/10.1002/anie.200903558
  18. 18. Arenas J.L., Crousse B. Eur. J. Org. Chem. 2021, 2021, 2665–2679. https://doi.org/10.1002/ejoc.202100327
  19. 19. Deng J., Wu Y.M., Chen Q.Y. Synthesis. 2005, 2730–2738. https://doi.org/10.1055/s-2005-872119
  20. 20. Gribanov P.S., Chesnokov G.A., Topchiy M.A., Asachenko A.F., Nechaev M.S. Org. Biomol. Chem. 2017, 15, 9575–9578. https://doi.org/10.1039/C7OB02091K
  21. 21. Carcenac Y., David-Quillot F., Abarbri M., Duchêne A., Thibonnet J. Synthesis. 2013, 45, 633–638. https://doi.org/10.1055/s-0032-1318112
  22. 22. Govdi A.I., Danilkina N.A., Ponomarev A.V., Balova I.A. J. Org. Chem. 2019, 84, 1925–1940. https://doi.org/10.1021/acs.joc.8b02916
  23. 23. Schulman J.M., Friedman A.A., Panteleev J., Lautens M. Chem. Commun. 2012, 48, 55–57. https://doi.org/10.1039/C1CC16110E
  24. 24. Kotovshchikov Y.N., Latyshev G.V., Beletskaya I.P., Lukashev N.V. Synthesis. 2018, 50, 1926–1934. https://doi.org/10.1055/s-0036-1591896
  25. 25. Szuroczki P., Sámson J., Kollár L. ChemistrySelect. 2019, 4, 5527–5530. https://doi.org/10.1002/slct.201900848
  26. 26. De Albuquerque D.Y., De Moraes J.R., Schwab R.S. Eur. J. Org. Chem. 2019, 2019, 6673–6681. https://doi.org/10.1002/ejoc.201901249
  27. 27. Gribanov P.S., Philippova A.N., Topchiy M.A., Minaeva L.I., Asachenko A.F., Osipov S.N. Molecules. 2022, 27, 1999. https://doi.org/10.3390/molecules27061999
  28. 28. Kotovshchikov Y.N., Tatevosyan S.S., Latyshev G.V., Kugusheva Z.R., Lukashev N.V., Beletskaya I.P. New J. Chem. 2023, 47, 12239–12247. https://doi.org/10.1039/D3NJ01264F
  29. 29. Li L., Shang T., Ma X., Guo H., Zhu A., Zhang G. Synlett. 2015, 26, 695–699. https://doi.org/10.1055/s-0034-1379970
  30. 30. do Nascimento J.E.R., Gonçalves L.C.C., Hooyberghs G., Van der Eycken E.V., Alves D., Lenardão E.J., Perin G., Jacob R.G. Tetrahedron Lett. 2016, 57, 4885–4889. https://doi.org/10.1016/j.tetlet.2016.09.027
  31. 31. Danilkina N.A., Govdi A.I., Balova I.A. Synthesis. 2020, 52, 1874–1896. https://doi.org/10.1055/s-0039-1690858
  32. 32. Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Erzunov D.A., Sokolova D.V., Beletskaya I.P., Lukashev N.V. J. Org. Chem. 2020, 85, 7863–7876. https://doi.org/10.1021/acs.joc.0c00520
  33. 33. Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Synthesis. 2022, 54, 369–377. https://doi.org/10.1055/a-1623-2333
  34. 34. Voloshkin V.A., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2022, 87, 7064–7075. https://doi.org/10.1021/acs.joc.2c00235
  35. 35. Kotovshchikov Y.N., Latyshev G.V., Navasardyan M.A., Erzunov D.A., Beletskaya I.P., Lukashev N.V. Org. Lett. 2018, 20, 4467−4470. https://doi.org/10.1021/acs.orglett.8b01755
  36. 36. Kotovshchikov Y.N., Latyshev G.V., Kirillova E.A., Moskalenko U.D., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2020, 85, 9015–9028. https://doi.org/10.1021/acs.joc.0c00931
  37. 37. Gevondian G.A., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2021, 86, 5639–5650. https://doi.org/10.1021/acs.joc.1c00115
  38. 38. Kotovshchikov Y.N., Sultanov R.H., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Org. Biomol. Chem. 2022, 20, 5764–5770. https://doi.org/10.1039/D2OB00909A
  39. 39. Barashkova X.A., Gevondian A.G., Latyshev G.V., Kotovshchikov Y.N., Bezzubov S.I., Lukashev N.V., Beletskaya I.P. Org. Lett. 2024, 26, 9625–9630. https://doi.org/10.1021/acs.orglett.4c03082
  40. 40. Гевондян А.Г., Котовщиков Ю.Н., Латышев Г.В., Лукашев Н.В., Белецкая И.П. ЖОрХ. 2023, 59, 1121–1130. @@Gevondian A.G., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Russ. J. Org. Chem. 2023, 59, 1465–1472. https://doi.org/10.1134/S1070428023090026
  41. 41. Galashev R.N., Latyshev G.V., Kotovshchikov Y.N., Lukashev N.V., Beletskaya I.P. Org. Biomol. Chem. 2025, 23, 4725–4729. https://doi.org/10.1039/d5ob00356c
  42. 42. Nusser B.D., Jenkins L.E., Lin X., Zhu L. J. Org. Chem. 2024, 89, 12610–12618. https://doi.org/10.1021/acs.joc.4c01533
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