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

Polina A. Nikitina; Никитина Полина Андреевна; Irina A. Oskina; Оськина Ирина Александровна; Elena B. Nikolaenkova; Николаенкова Елена Борисовна; Ekaterina A. Kulikova; Куликова Екатерина Андреевна; Vladimir S. Miroshnikov; Мирошников Владимир Сергеевич; Valery P. Perevalov; Перевалов Валерий Павлович; Alexey Ya. Tikhonov; Тихонов Алексей Яковлевич

doi:10.31857/S0514749225040144

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

作者: 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
隶属关系:
1. Mendeleev University of Chemical Technology of Russia
2. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the RAS
期: 卷 61, 编号 4 (2025)
页面: 475-483
栏目: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://ter-arkhiv.ru/0514-7492/article/view/689699
DOI: https://doi.org/10.31857/S0514749225040144
EDN: https://elibrary.ru/SEOHNP
ID: 689699

如何引用文章

全文:

开放存取

##reader.subscriptionAccessGranted##
受限制的访问

订阅或者付费存取

详细
全文:
作者简介
参考
补充文件
统计

详细

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.

关键词

alkylation, 1-hydroxyimidazoles, 1-benzylimidazoles, imidazole 3-oxides, benzyl halides

全文:

作者简介

Polina Nikitina

Mendeleev University of Chemical Technology of Russia

编辑信件的主要联系方式.
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0003-1542-5565
俄罗斯联邦, 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
俄罗斯联邦, 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
俄罗斯联邦, 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
俄罗斯联邦, 9, Miusskaya Sqr., Moscow, 125047

Vladimir Miroshnikov

Mendeleev University of Chemical Technology of Russia

Email: polinandrevna@yandex.ru
ORCID iD: 0000-0003-3815-7479
俄罗斯联邦, 9, Miusskaya Sqr., Moscow, 125047

Valery Perevalov

Mendeleev University of Chemical Technology of Russia

Email: polinandrevna@yandex.ru
ORCID iD: 0000-0002-3980-6496
俄罗斯联邦, 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
俄罗斯联邦, 9, Ac. Lavrentyev Ave., Novosibirsk, 630090

参考

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