Abstract
The report describes the synthesis of a series of new imidazolinones-2, imidazole-2-thiones, and 1,3-oxazoles based on the interaction of 1-bromo ketones containing a diterpene fragment with urea and thiourea. It is shown that the direction of the reaction and the yields of the products depend on the nature of the initial substrates and the conditions of the reaction. For instance, boiling bromides with ureas or thiourea in ethyl alcohol in the presence of sodium carbonate leads to nucleophilic substitution, forming diterpene-substituted ureas. Performing the same reaction in ethylene glycol at a temperature of 200–250°C in the presence of potassium hydroxide results in the formation of imidazolin-2-ones or -thiones containing the diterpene fragment at the 4-position with high yields.
REFERENCES
Antonova, M.M., Baranov, V.V., and Kravchenko, A.N., Chem. Heterocycl. Compd., 2015, vol. 51, no. 5, p. 395. https://doi.org/10.1007/s10593-015-1716-3
Kidwai, M., Bhatnagar, D., Mothsra, P., Singh, A.K., and Dey, S., J. Sulfur Chem., 2009, vol. 30, no. 1, p. 29. https://doi.org/10.1080/17415990802422365
Kulikov, A.S., Epishina, M.A., Fershtat, L.L., Romanova, A.A., and Makhova, N.N., Tetrahedron Lett., 2017, vol. 58, no. 42, p. 3998. https://doi.org/10.1016/j.tetlet.2017.09.014
Rajan, A. and Prakash, P., Tetrahedron Lett., 2017, vol. 58, no. 31, p. 3057. https://doi.org/10.1016/j.tetlet.2017.06.068
Safari, J., Abedi-Jazini, Z., Zarnegar, Z., and Sadeghi, M., Catal. Commun., 2016, vol. 77, p. 108. https://doi.org/10.1016/j.catcom.2016.01.007
de Santana, T.I., de Oliveira Barbosa, M., de Moraes Gomes, P.A.T., Cruz, A.C.N., Silva, T.G., and Leite, A.C.L., Eur. J. Med. Chem., 2018, vol. 144, p. 874. https://doi.org/10.1016/j.ejmech.2017.12.040
Sultanova, R.M., Lobov, A.N., Shumadalova, A.V., Meshcheryakova, S.A., Zileeva, Z.R., Khusnutdinova, N.S., Vakhitov, V.A., and Vakhitova, Y.V., Nat. Prod. Res., 2021, vol. 35, no. 8, p. 1340. https://doi.org/10.1080/14786419.2019.1648459
Yakupova, L.R., Nasibullina, R.A., Shamukaev, V.A., Sultanova, R.M., and Safiullin, R.L., Kin. Catal., 2020, vol. 61, no. 2, p. 232. https://doi.org/10.1134/S0023158420020123
Ostakhov, S.S., Sultanova, R.M., Masyagutova, G.A., and Khursan, S.L., High Energy Chem., 2020, vol. 54, no. 4, p. 241. https://doi.org/10.1134/S0018143920040104
Guernon, J.M. and Wu, Y.J., Tetrahedron Lett., 2011, vol. 52, p. 3633. https://doi.org/10.1016/j.tetlet.2011.05.028
Gursoy, A., Demirayak, S., Capan, G., Erol, K., and Vural, K., Eur. J. Med. Chem., 2000, vol. 35, p. 359. https://doi.org/10.1016/S0223-5234(00)00117-3
Vafina, G.F., Khanova, M.D., and Lobov, A.N., Chem. Nat. Compd., 2022, vol. 58, p. 1055. https://doi.org/10.1007/s10600-022-03865-w
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Translated by M. Chubarova
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Sultanova, R.M., Kuleshina, G.Z. & Khusnutdinova, N.S. Synthesis of 2-Phenyl-1,3-Oxazoles, 2-Imidazolinones, and 2-Imidazolinthiones Containing a Diterpene Fragment. rev. and adv. in chem. 13, 454–462 (2023). https://doi.org/10.1134/S2634827624600014
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DOI: https://doi.org/10.1134/S2634827624600014