Abstract
6,14,22-Triaryl-2,4,8,10,12,16,18,20,24-nonathia-6,14,22-triaza-1,3,9,11,17,19(1,4)-hexabenzocyclotetracosaphanes are synthesized in high yield and selectivity by cycloaminomethylation of 4,4′-thiodibenzenethiol with N,N-bis(methoxymethyl)-N-arylamines in the presence of a Sm(NO3)3·6H2O catalyst.
Similar content being viewed by others
References
Kuz’min, V.E., Lozitsky, V.P., Kamalov, G.L., Lozitskaya, R.N., Zheltvay, A.I., Fedtchouk, A.S., and Kryzhanovsky, D.N., Acta Biochim. Polonica, 2000, vol. 47, p. 867.
Gao, J., Ross Woolley, F., and Zingaro, R.A., J. Med. Chem., 2005, vol. 48, p. 7192. doi https://doi.org/10.1021/jm050497t
Lozytska, R., Kryzhanovsky, D., Mazepa, A., Gorodniuk, V., Kuz’min, V., Lozitsky, V., Fedchuck, A., Rybalko, S., Diadium, S., and Vanden Eynde, J.J., Arkivoc, 2004, vol. xiv, p. 118R. doi https://doi.org/10.3998/ark.5550190.0005.e13
Lehn, J.M., Pure Appl. Chem., 1979, vol. 51, p. 979.
Len, Zh.-M., Supramolekulyarnaya khimiya–masshtaby i perspektivy. Molekuly–supermolekuly–molekulyarnye ustroistva (Supramolecular Chemistry–Scales and Perspectives. Molecules–Supermolecules–Molecular Devices: Nobel Lecture), Moscow: Znanie, 1989.
Brooker, S., Eur. J. Inorg. Chem., 2002, p. 2535. doi https://doi.org/10.1002/1099-0682(200210)2002:10<2535::AIDEJIC2535>3.0.CO;2-Z
Martell, A.E., Perutka, J., and Kong, D., Coord. Chem. Rev., 2001, vol. 216–217, p. 55. doi https://doi.org/10.1016/S0010-8545(00)00407-0
Di Bella, S., Chem. Soc. Rev., 2001, vol. 30, p. 355. doi https://doi.org/10.1039/B100820J
Gallant, A.J., Hui, J.K.-H., Zahariev, F.E., Wang, Y.A., and MacLachlan, M.J., J. Org. Chem., 2005, vol. 70, p. 7936.
Voronkov, M.G. and Knutov, V.I., Russ. Chem. Rev., 1991, vol. 60, p. 1293. doi https://doi.org/10.1070/RC1991v060n12ABEH001147
Borisova, N.E., Reshetova, M.D., and Ustynyuk, Yu.A., Chem. Rev., 2007, vol. 107, p. 46. doi https://doi.org/10.1021/cr0683616
Houjou, H., Lee, S.-K., Hishikawa, Y., Nagawa, Y., and Hiratani, K., Chem. Commun., 2000, p. 2197. doi https://doi.org/10.1039/B005536K
Gromov, S.P., Dmitrieva, S.N., and Churakova, M.V., Russ. Chem. Rev., 2005, vol. 74, p. 461. doi https://doi.org/10.1070/RC2005v074n05ABEH001163
Elwahy, A.H.M. and Abbas, A.A., Tetrahedron, 2000, vol. 56, p. 885. doi https://doi.org/10.1016/S0040-4020(99)01068-6
Makhmudiyarova, N.N., Mudarisova, L.V., Meshcheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2015, vol. 71, p. 259. doi https://doi.org/10.1016/j.tet.2014.11.064
Makhmudiyarova, N.N., Khatmullina, G.M., Meshcheryakova, E.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Arkivoc, 2016, vol. iii, p. 48. doi https://doi.org/10.3998/ark.5550190.p009.364
Kukushkin, Yu.N., Reaktsionnaya sposobnost’ koordinatsionnykh soedinenii (Reactivity of Coordination Compounds), Leningrad: Khimiya, 1987.
Wellmar, U., J. Heterocycl. Chem., 1998, vol. 35, p. 1531. doi https://doi.org/10.1002/jhet.5570350653
Niatshina Z.T., Murzakova N.N., Vasilieva I.V., Rakhimova E.B., Akhmetova V.R., Ibragimov A.G., Dzhemilev U.M. Arkivoc, 2011, vol. viii, p. 141. doi https://doi.org/10.3998/ark.5550190.0012.810
Krohn, K. and Cludius-Brandt, S., Synthesis, 2010, p. 1344. doi https://doi.org/10.1055/s-0029-1218658
Abaev, V.T. and Serdyuk, O.V., Russ. Chem. Rev., 2008, v o l. 2, p. 1 7 7. d o i 1 0. 1 0 7 0 /RC2008v077n02ABEH003736
Borch, R.F. and Hassid, A.I., J. Org. Chem., 1972, vol. 37, p. 1673.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © N.N. Makhmudiyarova, G.M. Kiyamutdinova, L.S. Koroleva, A.G. Ibragimov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1649–1652.
Rights and permissions
About this article
Cite this article
Makhmudiyarova, N.N., Kiyamutdinova, G.M., Koroleva, L.S. et al. Efficient Synthesis of N-Aryl-substituted Nonathiatriaza-(1,4)-hexabenzocyclotetracosaphanes. Russ J Org Chem 54, 1660–1664 (2018). https://doi.org/10.1134/S1070428018110064
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018110064