Skip to main content
Log in

Synthesis of 5-Aryl-1,2,3,4-tetrahydrobenzo[a]phenanthridines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, 1H NMR, and mass spectra of the synthesized compounds were discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Belousova, A.K., Blokhin, N.N., Borisov, V.I., Gauze, G.F., Giller, S.A., Gorbacheva, L.B., Dudnik, Yu.V., Lidak, M.Yu., Lorie, Yu.I., Lukevits, E.Ya., Perevodchi-kova, N.I., Sof'ina, Z.P., and Syrkin, A.B., Khimioterapiya zlokachestvennykh opukholei (Chemotherapy of Malignant Tumors), Moscow: Meditsina, 1977.

    Google Scholar 

  2. Lee, Cheur-Man, J. Med. Chem., 1968, vol. 11, no. 2, pp. 388-392.

    Google Scholar 

  3. Rubtsov, M.V., J. Med. Pharm. Chem., 1960, vol. 2, pp. 113-115.

    Google Scholar 

  4. Dyson, G.M. and May, P., May's Chemistry of Synthetic Drugs, London: Longmans, 1959.

    Google Scholar 

  5. Smidrekal, J., Collect. Czech. Chem. Commun., 1988, vol. 53, pp. 3186-3187.

    Google Scholar 

  6. Wang, L.K., Johnson, R.K., and Hecht, S.M., Chem. Res. Toxicol., 1993, vol. 6, pp. 813-818.

    Google Scholar 

  7. Watts, W.J., Lawler, C.P., and Knoerzer, T., Eur. J. Pharmacol., 1993, vol. 239, pp. 271-276.

    Google Scholar 

  8. Martines, R., Toscano, R., Lingaza, J.E., and Sanchez, H., J. Heterocycl. Chem., 1992, vol. 29, pp. 1385-1389.

    Google Scholar 

  9. Henry, T.A., The Plant Alkaloids, London, 1949, 4th ed. Translated under the title Khimiya rastitel'-nykh alkaloidov, Moscow: Goskhimizdat, 1965, p. 547.

  10. Jpn. Patent 20 862, 1965, Ref. Zh. Khim., 1968, 19N395.

  11. Kozlov, N.S., Vorob'eva, G.V., and Bychkova, G.S., Izv. Akad. Nauk BSSR, Ser. Khim. Nauk, 1969, no. 5, pp. 80-86.

  12. Organic Reactions, Adams, R., Ed., New York: Wiley, 1953, vol. 7. Translated under the title Organicheskie reaktsii, Moscow: Inostrannaya Literatura, 1956, vol. 7, pp. 100-139.

    Google Scholar 

  13. Kozlov, N.S. and Vorob'eva, G.V., Izv. Akad. Nauk BSSR, Ser. Khim. Nauk, 1970, no. 5, pp. 91-93.

  14. Technique of Organic Chemistry, Weissberger, A., Ed., vol. XI, Elucidation of Structures by Physical and Chemical Methods, New York: Interscience, 1963. Translated under the title Ustanovlenie struktury organicheskikh soedinenii fizicheskimi i khimicheskimi metodami, Moscow: Khimiya, 1967, vol. 1, p. 179.

  15. Kozlov, N.S. and Vorob'eva, G.V., Khim. Geterotsikl. Soedin., 1971, no. 4, pp. 519-523.

  16. Rao, C.N.R., Ultra-Violet and Visible Spectroscopy Chemical Applications, London: Butterworth, 1961.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kozlov, N.G., Basalaeva, L.I. Synthesis of 5-Aryl-1,2,3,4-tetrahydrobenzo[a]phenanthridines. Russian Journal of General Chemistry 71, 250–256 (2001). https://doi.org/10.1023/A:1012355506689

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012355506689

Keywords

Navigation