Abstract
Short-term heating of a mixture of tryptamine, aromatic aldehyde, and methyl 4-(4-fluorophenyl)-2,4-dioxobutanoate, followed by keeping for a day at room temperature, leads to the formation of 5-aryl-1-[2-(1H-indol-3-yl)-ethyl]-4-[(4-fluorophenyl)(hydroxy)methylene]pyrrolidine-2,3-diones. Structure of the obtained compounds was confirmed by IR and NMR spectroscopy methods.
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REFERENCES
Saurav, K. and Kannabiran, K., Saudi J. Biol. Sci., 2012, vol. 19, no. 1, p. 81. https://doi.org/10.1016/j.sjbs.2011.07.003
Gein, V.L., Kasimova, N.N., Chaschina, S.V., Starkova, A.V., and Yankin, A.N., Russ. J. Gen. Chem., 2020, vol. 90, no. 2, p. 202. https://doi.org/10.31857/S0044460X20020067
Ramachandran, G., Karthikeyan, N.S., Giridharan, P., and Sathiyanarayanan, K.I., Org. Biomol. Chem., 2012, vol. 10, no. 28, p. 5343. https://doi.org/10.1039/c2ob25530h
Malawska, B., Kulig, K., Filipek, B., Sapa, J., Maciąg, D., Zygmunt, M., and Antkiewicz-Michaluk, L., Eur. J. Med. Chem., 2002, vol. 37, no. 3, p. 183. https://doi.org/10.1016/s0223-5234(01)01321-6
Ikuta, H., Shirota, H., Kobayashi, S., Yamagishi, Y., Yamada, K., Yamatsu, I., and Katayama, K., J. Med. Chem., 1987, vol. 30, no. 11, p. 1995. https://doi.org/10.1021/jm00394a011
Coutrot, P., Claudel, S., Didierjean, C., and Grison, C., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 2, p. 417. https://doi.org/10.1016/j.bmcl.2005.09.068
Baures, P.W., Eggleston, D.S., Erhard, K.F., Cieslinski, L.B., Torphy, T.J., and Christensen, S.B., J. Med. Chem., 1993, vol. 36, no. 22, p. 3274. https://doi.org/10.1021/jm00074a007
Heinrich, D.M., Flanagan, J.U., Jamieson, S.M.F., Silva, S., Rigoreau, L.J.M., Trivier, E., Raynham, T., Turnbull, A.P., and Denny, W.A., Eur. J. Med. Chem., 2013, vol. 62, p. 738. https://doi.org/10.1016/j.ejmech.2013.01.047
Gein, V.L., Varkentin, L.I., Kazantseva, M.I., Dmitriev, M.V., and Yankin, A.N., Russ. J. Gen. Chem., 2019, vol. 89, no. 11, p. 2156. https://doi.org/10.1134/S1070363219110057
Gein, V.L., Nosova, N.V., Yankin, A.N., Bazhina, A.Y., and Dmitriev, M.V., Polycyclic Aromatic Compd., 2019, p. 540 https://doi.org/10.1080/10406638.2019.1602061
Yankin, A.N., Nosova, N.V., Dmitriev, M.V., and Gein, V.L., Russ. J. Org. Chem., 2016, vol. 52, no. 2, p. 206. https://doi.org/10.1134/S107042801602007X
Dai, L., Shu, P., Wang, Z., Li, Q., Yu, Q., Shi, Y., and Rong, L., Synthesis, 2017, no. 49. P.637. https://doi.org/10.1055/s-0036-1588605
Hong, A.Y. and Vanderwall, C.D., Tetrahedron, 2017, no. 73, p. 4160. https://doi.org/10.1016/j.tet.2016.11.004
Guistiano, M., Pellicia, S., Sangaletti, L., Meneghetti, F., Amato, J., Novellino, E., and Tron Gian, C., Tetrahedron Lett., 2017, no. 58, p. 4264. https://doi.org/10.1016/j.tetlet.2017.09.076
Singh, V.K., Dubey, R., Upadhyay, A., Sharma, L.K., and Singh, R.K.P., Tetrahedron Lett., 2017, no. 58, p. 4227. https://doi.org/10.1016/j.tetlet.2017.09.003
Nasakin, O.E., Kasantseva, M.I., Varkentin, L.I., and Gein, V.L., Russ. J. Gen. Chem., 2018, vol. 88, no. 6, p. 1270. https://doi.org/10.1134/S1070363218080167
Gein, V.L., Kasantseva, M.I., Varkentin, L.I., Zamaraeva, T.M., Yankin, A.N., Beletskii, E.V., and Novikova, V.V., Russ. J. Gen. Chem., 2020, vol. 90, no. 8, p. 1426. https://doi.org/10.1134/S1070363220080083
Yaxue, Z., Qing, W., Qingqing, M., Dazhong, D., Huaiyu, Y., Guangwei, G., Dawei, L., Weiliang, Z., and Huchen, Z., Bioorg. Med. Chem., 2012, no. 20, p. 1240. https://doi.org/10.1016/j.bmc.2011.12.035
Tongquing, L., Ning, Y., Hongbo, L., Jianfeng, P., and Luhua, L., Med. Chem. Lett., 2016. https://doi.org/10.1021/acsmedchemlett.5b00420
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This work was financially supported by the Perm Scientific and Educational Center “Rational Subsoil Use” (2022).
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Kazantseva, M.I., Zamaraeva, T.M. & Gein, V.L. Synthesis of Pyrrolidine-2,3-dione Derivatives by Reacting Methyl 4-(4-Fluorophenyl)-2,4-dioxobutanoate with Tryptamine and Aromatic Aldehydes. Russ J Gen Chem 92, 949–954 (2022). https://doi.org/10.1134/S1070363222060056
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DOI: https://doi.org/10.1134/S1070363222060056