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

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Дәйексөз келтіру

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Аннотация

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.

Толық мәтін

Рұқсат жабық

Авторлар туралы

Polina Nikitina

Mendeleev University of Chemical Technology of Russia

Хат алмасуға жауапты Автор.
Email: polinandrevna@yandex.ru
ORCID iD: 0000-0003-1542-5565
Ресей, 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
Ресей, 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
Ресей, 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
Ресей, 9, Miusskaya Sqr., Moscow, 125047

Vladimir Miroshnikov

Mendeleev University of Chemical Technology of Russia

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

Valery Perevalov

Mendeleev University of Chemical Technology of Russia

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

Әдебиет тізімі

  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. 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. 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. 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. 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. 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. 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. 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. 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. Nikitina P.A., Koldaeva T.Yu., Zakharko M.A., Perevalov V.P. Aust. J. Chem., 2020, 73, 1098–1104. doi: 10.1071/CH20044
  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. 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. 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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4. Scheme 3

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5. Scheme 4

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