The possibility of a direct phenylation of benzoquinoline nitrogen atom with nucleogenic phenyl cations has been demonstrated. A simple method has been developed for obtaining previously unknown tritium labeled N-phenyl derivatives of benzo[h]quinolinium, which are promising radioactive markers for studying the biological action mechanisms of medicinal substances containing the benzoquinolinium structure.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. R. Katritzky and C. W. Rees (editors), Comprehensive Heterocyclic Chemistry, Vol. 1, Pergamon, Oxford (1984), p. 143.
E. Lukevics, Khim. Geterotsikl. Soedin., 723 (1995). [Chem. Heterocycl. Compd., 31, 639 (1995).]
P. Kapkova, N. Stiefl, U. Surig, B. Engels, K. Baumann, and U. Holzgrabe, Arch. Pharm., 336, 523 (2003).
E. S. Krichevskii, L. M. Alekseeva, V. A. Parshin, M. A. Kalinkina, V. V. Chernyshev, and V. G. Granik, Khim.-Farm. Zh., No. 10, 9 (2007).
D. Levy and Y. Ashani, Biochem. Pharmacol., 35, 1079 (1986).
R. Sanchez-Martin, J. M. Campos, A. Conejo-Garcia, O. Cruz-López, M. Báñez-Coronel, A. Rodríguez-González, M. A. Gallo, J. C. Lacal, and A. Espinosa, J. Med. Chem., 48, 3354 (2005).
P. Srivani and G. N. Sastry, J. Mol. Graphics Modell., 27, 676 (2009).
W. S. Chen, G. H. Cocolas, C. J. Cavallito, and K. J. Chai, J. Med. Chem., 20, 1617 (1977).
W. S. Chen, G. H. Cocolas, and C. J. Cavallito, J. Pharm. Sci., 68, 1025 (1979).
J. DePriest, G. Y. Zheng, C. Woods, D. P. Rillema, N. A. Mikirova, and M. E. Zandler, Inorg. Chim. Acta, 264, 287 (1997).
M. A. Loza-Mejía, S. Olvera-Vázquez, K. Maldonado-Hernández, T. Guadarrama-Salgado, I. González-Sanchez, F. Rodríguez-Hernández, J. D. Solano, R. Rodríguez-Sotres, and A. Lira-Rocha, Bioorg. Med. Chem., 17, 3266 (2009).
K. H. Pausacker, Aust. J. Chem., 11, 200 (1958).
F. Brody and P. R. Ruby in: A. Klingsberg (editor), Pyridine and Its Derivatives, Part 1, Interscience, New York (1960), p. 474.
N. E. Shchepina, V. V. Avrorin, G. A. Badun, G. A. Aleksandrova, S. E. Ukhanov, V. M. Fedoseev, S. B. Lewis, and I. I. Boiko, Khim. Geterotsikl. Soedin, 1008 (2009). [Chem. Heterocycl. Compd., 45, 796 (2009)].
N. E. Shchepina, V. V. Avrorin, G. A. Badun, S. B. Lewis, V. M. Fedoseev, and S. E. Ukhanov, Vestn. Mosk. Gos. Univ., Ser. 2, Khimiya, 50, 311 (2009).
N. E. Shchepina, V. V. Avrorin, G. A. Badun, V. M. Fedoseev, and S. B. Lewis, Khim. Geterotsikl. Soedin., 692 (2010). [Chem. Heterocycl. Compd., 46, 547 (2010).]
N. E. Shchepina, V. V. Avrorin, G. A. Aleksandrova, and G. A. Badun, Perspektivnye Materialy, 10, 339 (2011).
N. E. Shchepina, V. V. Avrorin, G. A. Badun, S. B. Lewis, and S. E. Ukhanov, Khim. Geterotsikl. Soedin., 320 (2012). [Chem. Heterocycl. Compd., 48, 301 (2012).]
N. E. Shchepina, I. I. Boiko, and G. A. Aleksandrova, Khim.-Farm. Zh., 45, No. 3, 30 (2011).
G. T. Pilyugin and E. P. Opanasenko, Ukr. Khim. Zh., 18, 625 (1952).
G. T. Pilyugin and E. P. Opanasenko, Zh. Obshch. Khim., 27, 1015 (1957).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1282–1286, August, 2012.
Rights and permissions
About this article
Cite this article
Shchepina, N.E., Avrorin, V.V., Badun, G.A. et al. Preparation of N-phenylbenzo[h]quinolinium derivatives labeled with tritium. Chem Heterocycl Comp 48, 1196–1199 (2012). https://doi.org/10.1007/s10593-012-1121-0
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-012-1121-0