Email this article Alkylation of Ethyl 2-Aryl-1-hydroxy-4-methyl-1Н-imidazole-5-carboxylates with Benzyl Halides
- Authors: Nikitina P.A.1, Oskina I.A.2, Nikolaenkova E.B.2, Kulikova E.A.1, Miroshnikov V.S.1, Perevalov V.P.1, Tikhonov A.Y.2
-
Affiliations:
- Mendeleev University of Chemical Technology of Russia
- Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
- Issue: Vol 61, No 4 (2025)
- Pages: 475-483
- Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
- URL: https://rjpbr.com/0514-7492/article/view/689699
- DOI: https://doi.org/10.31857/S0514749225040144
- EDN: https://elibrary.ru/SEOHNP
- ID: 689699
Cite item
Open Access
Access granted
Abstract
Alkylation of ethyl 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates with substituted benzyl halides 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-hydroxyphenyl moiety was present in position 2 of imidazole ring, then monoalkylation proceeded selectively at hydroxy group of the nitrogen atom of heterocycle.
Full Text
About the authors
Polina A. Nikitina
Mendeleev University of Chemical Technology of Russia
Author for correspondence.
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0003-1542-5565
Russian Federation, 9, Miusskaya Sqr., Moscow, 125047
Irina A. Oskina
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0001-5788-0182
Russian Federation, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
Elena B. Nikolaenkova
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID iD: 0009-0000-5034-8513
Russian Federation, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
Ekaterina A. Kulikova
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID iD: 0009-0009-2311-395X
Russian Federation, 9, Miusskaya Sqr., Moscow, 125047
Vladimir S. Miroshnikov
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0003-3815-7479
Russian Federation, 9, Miusskaya Sqr., Moscow, 125047
Valery P. Perevalov
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0002-3980-6496
Russian Federation, 9, Miusskaya Sqr., Moscow, 125047
Alexey Ya. Tikhonov
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0002-6391-4366
Russian Federation, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
References
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Nikitina P.A., Koldaeva T.Yu., Zakharko M.A., Perevalov V.P. Aust. J. Chem., 2020, 73, 1098–1104. doi: 10.1071/CH20044
- 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
- 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
- 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
Supplementary files
