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

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

Alkylation of Ethyl 2-Aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates with Benzyl Halides

PII
S30346304S0514749225040144-1
DOI
10.7868/S3034630425040144
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 4
Pages
475-483
Abstract
Alkylation of ethyl 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates with substituted benzyl hal-ides led to the selective formation of O-alkoxy derivatives. Products of N-alkylation(1-alkylimidazole 3-oxides) could be obtained by condensation reaction from acyclic starting compounds. If a 2-hydroxy-phenyl moiety was present in position 2 of imidazole ring, then monoalkylation proceeded selectively at hydroxy group of the nitrogen atom of heterocycle.
Keywords
алкилирование 1-гидроксиимидазолы 1-бензилоксиимидазолы 3-оксиды имидазола бензилгалогениды
Date of publication
13.12.2025
Year of publication
2025
Number of purchasers
0
Views
24

References

  1. 1. Chen S., Zhang T., Wang T., Wang J., Wang F., Niu H., Wu C., Wang S. Eur. J. Med. Chem. 2015, 103, 343–353. doi 10.1016/j.ejmech.2015.08.056
  2. 2. Zhang T., Lv Y., Lei Y., Liu D., Feng Y., Zhao J., Chen S., Meng F., Wang S. Eur. J. Med. Chem. 2018, 146, 668–677. doi 10.1016/j.ejmech.2018.01.060
  3. 3. da Silva R.B., Loback V.B., Salomão K., de Castro S.L., Wardell J.L., Wardell S.M.S.V., Costa T.E.M.M., Penido C., Henriques M.G.M.O., Carvalho S.A., da Silva E.F., Fraga C.A.M. Molecules. 2013, 18, 3445–3457. doi 0.3390/molecules18033445
  4. 4. Lei Y., Zhang B., Liu D., Zhao J., Dai X., Gao J., Mao Q., Feng Y., Zhao J., Lin F., Duan Y., Zhang Y., Bao Z., Yang Y., Mou Y., Wang S. J. Med Chem. 2020, 63, 15752–15772. doi 10.1021/acs.jmedchem.0c01524
  5. 5. Lei Y., Zhang B., Zhang Y., Dai X., Duan Y., Mao Q., Gao J., Yang Y., Bao Z., Fu X., Ping K., Yan C., Mou Y., Wang S. Eur. J. Med. Chem. 2021, 220, 113437. doi 10.1016/j.ejmech.2021.113437
  6. 6. Никитина П.А., Бормотов Н.И., Шишкина Л.Н., Тихонов А.Я., Перевалов В.П. Изв. АН. Сер. хим. 2019, 634–637. @@Nikitina P.A., Bormotov N.I., Shishkina L.N., Tikhonov A.Ya., Perevalov V.P. Russ. Chem. Bull., Int. Ed. 2019, 68, 634–637. doi 10.1007/s11172-019-2467-6
  7. 7. Nikitina P.A., Basanova E.I., Nikolaenkova E.B., Os’kina I.A., Serova O.A., Bormotov N.I., Shishkina L.N., Perevalov V.P., Tikhonov A.Ya. Bioorg. Med. Chem. Lett. 2023, 79, 129080. doi 10.1016/j.bmcl.2022.129080
  8. 8. Laus G., Schwärzler A., Bentivoglio G., Hummel M., Kahlenberg V., Wurst K., Kristeva E., Schütz J., Kopacka H., Kreutz C., Bonn G., Andriyko Y., Nauer G., Schottenberger H. Z. Naturforsch. 2008, 63b, 447–464. doi 10.1515/znb-2008-0411
  9. 9. Nikitina P.A., Peregudov A.S., Koldaeva T.Yu., Kuz’mina L.G., Adiulin E.I., Tkach I.I., Perevalov V.P. Tetrahedron. 2015, 71, 5217–5228. doi 10.1016/j.tet.2015.06.032
  10. 10. Nikitina P.A., Koldaeva T.Yu., Zakharko M.A., Perevalov V.P. Aust. J. Chem., 2020, 73, 1098–1104. doi 10.1071/CH20044
  11. 11. Оськина И.А., Тихонов А.Я. ЖОрХ. 2020, 56, 303–306. @@Os’kina I.A., Tikhonov A.Ya. Russ. J. Org. Chem. 2020, 56, 339–342. doi 10.1134/S107042802001027X
  12. 12. Никитина П.А., Перевалов В.П. ХГС. 2017, 53, 123–149. @@Nikitina P.A., Perevalov V.P. Chem. Heterocycl. Compd. 2017, 53, 123–149. doi 10.1007/s10593-017-2030-z
  13. 13. Nikitina P.A., Kuz'mina L.G., Perevalov V.P., Tkach I.I. Tetrahedron. 2013, 69, 3249–3256. doi 10.1016/j.tet.2013.02.039
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