Abstract
Efficient methods of the synthesis of cyclophanes containing the thiourea moiety via the reaction of o-, m-, and p-aminobenzamides with 1,3-bis(dimethylaminomethyl)thiourea or 1,3-bis(methoxymethyl)thiourea using NiCl2·6H2O and SmCl3·6H2O as catalysts have been developed.
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Petersen, H., Syntesis, 1973, vol. 5, p. 243. doi https://doi.org/10.1055/s-1973-22190
Garibov, E.N., Rzaeva, I.A., Shykhaliev, N.G., Kuliev, A.I., Farzaliev, V.M., and Allakhverdiev, M.A., Russ. J. Appl. Chem., 2010, vol. 83, no. 4, p. 707. doi https://doi.org/10.1134/S1070427210040245
El-Shamy, I.E., Abdel-Mohsen, A.M., Alsheikh, A.A., Fouda, M.M.G., Al-Deyab, S.S., El-Hashash, M.A., and Jancar, J., Dyes and Pigments, 2015, vol. 113, p. 357. doi https://doi.org/10.1016/j.dyepig.2014.08.026
Ertan, M., Tayhan, A.B., and Yulug, N., Arch. Pharm., 1990, vol. 323, p. 605. doi 10.1002ardp.19903230910
Gullapelli, K., Brahmeshwari, G., Ravichander, M., and Kusuma, U., Egypt. J. Basic Appl. Sci., 2017, vol. 4, p. 303. doi https://doi.org/10.1016/j.ejbas.2017.09.002
Martinovich, Yu.A., Ramsh, S.M., Hamoud, F., Fundamenskii, V.S., Gurzhii, V.V., Zakharov, V.I., and Khrabrova, E.S., Russ. J. Org. Chem., 2018, vol. 54, no. 6, p. 878. doi https://doi.org/10.1134/S107042801806009X
Kaye, P.T. and Nocanda, X.W., Arkivoc, 2000, vol. 6, p. 930.
Sasaki Sh.-ichi, Mizuno, M., Naemura, K., and Tobe, Yo, J. Org. Chem., 2000, vol. 65, no. 2, p. 275. doi https://doi.org/10.1021/jo991237k
Kabha, E., Jacquement, C., Pembouong, G., Mignet, N., Scherman, D., and Herscovici, J., Bioorg. Med. Chem., 2008, vol. 16, p. 4003. doi https://doi.org/10.1016/j.bmc.2008.01.029
Farzaliev, V.M., Allakhverdiev, M.A., Magerramov, A.M., Shirinova, N.A., Dzavadova, L.A., Rzaeva, I.A., Khalilova, A.Z., and Aliev, F.Y., Russ. J. Appl. Chem., 2001, vol. 74, no. 1, p. 114. doi https://doi.org/10.1023/A:1012764404658
Walter, A.M. and Heilmayer, L., Antibiotika Fibel, Stuttgart: Thieme Verlag, 1965, p. 419.
Kiyokawa, Sh., Hirata, Y., Nagaoka, Y., Shibano, M., Taniguchi, M., Yasuda, M., Baba, K., and Uesato, Sh., Bioorg. Med. Chem., 2010, vol. 18, p. 3925. doi https://doi.org/10.1016/j.bmc.2010.04.033
Cai, J., Wei, H., Hong, K.H., Wu, X., Cao, M., Zong, X., Li, L., Sun, C., Chen, J., and Ji, M., Eur. J. Med. Chem., 2015, vol. 96, p. 1. doi https://doi.org/10.1016/j.ejmech.2015.04.002
Caldini, R., Fanti, E., Magnelli, L., Barletta, E., Tanganelli, E., Zampieri, M., and Chevanne, M., Vascular Cell., 2011, vol. 3, p. 12. doi https://doi.org/10.1186/2045-824X-3-12
Mabkhot, Y.N., Al-Majid, A.M., Barakat, A., Al-Showiman, S.S., Al-Har, M.S., Radi, S., Naseer, M.M., and Hadda, T.B., Int. J. Mol. Sci., 2014, vol. 15, p. 1503. doi https://doi.org/10.3390/ijms15035115
McKerrecher, D., Allen, J.V., Caulkett, P.W.R., Donald, C.S., Fenwick, M.L., Grange, E., Johnson, K.M., Johnstone, C., Jones, C.D., Pike, K.G., Rayner, J.W., and Walker, R.P., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 2705. doi https://doi.org/10.1016/j.bmcl.2006.02.022
Nishimura, T., Iino, T., Mitsuya, M., Bamba, M., Watanabe, H., Tsukahara, D., Kamata, K., Sasaki, K., Ohyama, S., Hosaka, H., Futamura, M., Nagata, Y., and Eiki Junichi, Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 1357. doi https://doi.org/10.1016/j.bmcl.2009.01.053
More, P., Patil, A., and Salunkhe, R., RSC Adv., 2014, vol. 96, no. 4, p. 63039. doi https://doi.org/10.1039/c4ra09514f
Khairullina, R.R., Geniyatova, A.R., Ibragimov, A.G., and Dzemilev, U.M., Russ. J. Org. Chem., 2013, vol. 49, no. 6, p. 904. doi https://doi.org/10.1134/S1070428013060171
Khairullina, R.R., Geniyatova, A.R., Ibragimov, A.G., and Dzemilev, U.M., Chem. Heterocl. Compd., 2014, vol. 50, no. 5, p. 715. doi https://doi.org/10.1007/s10593-014-1525-0
Khairullina, R.R., Geniyatova, A.R., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzemilev, U.M., Russ. J. Org. Chem., 2015, vol. 51, no. 1, p. 116. doi https://doi.org/10.1134/S1070428015010200
Khairullina, R.R., Tyumkina, T.V., Geniyatova, A.R., Mullagil’dina, F.K., and Ibragimov, A.G., Russ. J. Gen. Chem., 2019, vol. 89, no. 2, p. 202. doi https://doi.org/10.1134/S0044460X19020069
Khairullina, R.R., Geniyatova, A.R., Tyumkina, T.V., Karamzina, D.S., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2017, vol. 73, no. 50, p. 7079. doi https://doi.org/10.1016/j.tet.2017.10.068
Tramontini, M. and Angiolini, L., Tetrahedron, 1990, vol. 46, p. 1791. doi https://doi.org/10.1016/S0040-4020(01)89752-0
Tramontini, M., Synthesis, 1973, no. 12, p. 703. doi https://doi.org/10.1055/s-1973-22294
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Khairullina, R.R., Tyumkina, T.V., Geniyatova, A.R. et al. Catalytic Cycloaminomethylation of Aminobenzamides with 1,3-Bis[dimethylamino(methoxy)methyl]thiourea. Russ J Gen Chem 89, 378–384 (2019). https://doi.org/10.1134/S1070363219030022
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DOI: https://doi.org/10.1134/S1070363219030022