Abstract
Structure of two 4-aryl-1-trichloromethylisoquinolines as well as 3-dichloromethyl-6-phenyl-1,2,4-triazine (a synthetic precursor of the corresponding isoquinoline) has been studied by single-crystal X-ray diffraction analysis. The effect of the nature of substituents in the heterocycles on their crystal structure has been shown. The effect of acceptor di- and trichloromethyl groups on the nature of intermolecular interactions realized in crystals has been demonstrated.
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REFERENCES
Primas, N., Suzanne, P., Verhaeghe, P., Hutter, S., Kieffer, C., Laget, M., Cohen, A., Broggi, J., Lancelot, J.-C., Lesnard, A., Dallemagne, P., Rathelot, P., Rault, S., Vanelle, P., and Azas, N., Eur. J. Med. Chem., 2014, vol. 83, p. 26. https://doi.org/10.1016/j.ejmech.2014.06.014
Song, W., Wan, M., Li, S., Zhang, L., Wang, X., and Jia, Z., CN Patent 108727397 A, 2018.
Zhou, Y., Wu, C., Dong, X., and Qu, J., J. Org. Chem., 2016, vol. 81, p. 5202. https://doi.org/10.1021/acs.joc.6b00885
Nikonov, I.L., Slepukhin, P.A., Kopchuk, D.S., Kovalev, I.S., Zyryanov, G.V., Suvorova, A.I., Eltsov, O.S., Rusinov, V.L., and Chupakhin, O.N., Chem. Heterocycl. Compds., 2019, vol. 55, no. 11, p. 1124. https://doi.org/10.1007/s10593-019-02588-1
Kozhevnikov, D.N., Kataeva, N.N., Rusinov, V.L., and Chupakhin, O.N., Russ. Chem. Bull., 2004, vol. 53, p. 1295. https://doi.org/10.1023/B:RUCB.0000042289.07168.8f
Fen, H.-K., Chantrapromma, S., Maity, A.C., and Goswami, S.,Acta Crystallogr. (E), 2010, vol. 66, p. 424. https://doi.org/10.1107/S1600536810002035
Xie, M.-H., Liu, Y.-L., Zou, P., He, Y.-J., and Huang, B.,Acta Crystallogr. (E), 2010, vol. 66, p. 5. https://doi.org/10.1107/S1600536809051071
Sopková-de Oliveira Santos, J., Verhaeghe, P., Lohier, J.-F., Rathelot, P., Vanelle, P., and Rault, S., Acta Crystallogr. (C), 2008, vol. 64, p. 441. https://doi.org/10.1107/S0108270108020374
Kaluski, Z. and Golankiewicz, K., Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1965, vol. 13, p. 93.
Fun, H.-K., Chantrapromma, S., Maity, A.C., and Goswami, S.,Acta Crystallogr. (E), 2010, vol. 66, p. 622. https://doi.org/10.1107/S1600536810005234
Iaroshenko, V.O., Mkrtchyan, S., Ghazaryan, G., Hakobyan, A., Maalik, A., Supe, L., Villinger, A., Tolmachev, A., Ostrovskyi, D., Sosnovskikh, V.Ya., Ghochikyan, T.V., and Langer, P., Synthesis, 2011, p. 469. https://doi.org/10.1055/s-0030-1258364
Sipyagin, A.M. and Aliev, Z.G., Chem. Heterocycl. Compd., 1993, vol. 29, no. 11, p. 1287. https://doi.org/10.1007/BF00532026
Mercury CSD, ver. 3.10.3, release 2018.
Bondi, A., J. Phys. Chem., 1964, vol. 68, p. 441. https://doi.org/10.1021/j100785a001
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
Sheldrick, G.M., Acta Cryst., 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930
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This study was financially supported by the Russian Science Foundation (grant no. 18-13-00365).
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Slepukhin, P.A., Nikonov, I.L., Kopchuk, D.S. et al. X-Ray Diffraction Structural Studies of a Series of 4-Aryl-1-di- and 4-Aryl-1-trichloromethylisoquinolines and Their 1,2,4-Triazine Precursors. Russ J Gen Chem 90, 1192–1196 (2020). https://doi.org/10.1134/S1070363220070038
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DOI: https://doi.org/10.1134/S1070363220070038