Enviar artigo por via de e-mail Alkylation of Ethyl 2-Aryl-1-hydroxy-4-methyl-1Н-imidazole-5-carboxylates with Benzyl Halides
- Autores: 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
-
Afiliações:
- Mendeleev University of Chemical Technology of Russia
- Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
- Edição: Volume 61, Nº 4 (2025)
- Páginas: 475-483
- Seção: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
- URL: https://freezetech.ru/0514-7492/article/view/689699
- DOI: https://doi.org/10.31857/S0514749225040144
- EDN: https://elibrary.ru/SEOHNP
- ID: 689699
Citar
Texto integral
Acesso aberto
Acesso está concedido
Acesso é pago ou somente para assinantes
Resumo
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.
Palavras-chave
Texto integral
Sobre autores
Polina Nikitina
Mendeleev University of Chemical Technology of Russia
Autor responsável pela correspondência
Email: polinandrevna@yandex.ru
ORCID ID: 0000-0003-1542-5565
Rússia, 9, Miusskaya Sqr., Moscow, 125047
Irina Oskina
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID ID: 0000-0001-5788-0182
Rússia, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
Elena Nikolaenkova
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID ID: 0009-0000-5034-8513
Rússia, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
Ekaterina Kulikova
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID ID: 0009-0009-2311-395X
Rússia, 9, Miusskaya Sqr., Moscow, 125047
Vladimir Miroshnikov
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID ID: 0000-0003-3815-7479
Rússia, 9, Miusskaya Sqr., Moscow, 125047
Valery Perevalov
Mendeleev University of Chemical Technology of Russia
Email: polinandrevna@yandex.ru
ORCID ID: 0000-0002-3980-6496
Rússia, 9, Miusskaya Sqr., Moscow, 125047
Alexey Tikhonov
Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
Email: polinandrevna@yandex.ru
ORCID ID: 0000-0002-6391-4366
Rússia, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090
Bibliografia
- 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
Arquivos suplementares
