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Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene

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Abstract

N-Arylmethylene-2-naphthylamines react with acetylcyclohexane and 1-acetylcyclohexene under mild conditions to afford 2-aryl-2-(2-naphthylamino)ethyl cyclohexyl and 1-cyclohexenyl ketones, respectively. Under more severe conditions (110°C), the reaction is accompanied by cyclization with formation of 3-aryl-1-cyclohexyl(or 1-cyclohexenyl)benzo[f]quinolines. Proper choice of the amount of catalyst, temperature, and reaction time allows isolation of intermediate 3-aryl-1-cyclohexyl(or 1-cyclohexenyl)-3,4-dihydrobenzo[f]quinolines.

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REFERENCES

  1. Smidrkal, J., Coll. Czech. Chem. Commun., 1988, vol. 53, no.12, p. 3186.

    Google Scholar 

  2. Wang, L.K., Johnson, K., and Hecht, S.M., Chem. Res. Toxicol., 1993, vol. 6, p. 813.

    Google Scholar 

  3. Watts, W.J., Lawler, S.R., and Knoerzer, T., Eur. J. Pharmacol., 1993, vol. 239, p. 271.

    Google Scholar 

  4. Dweik, H.S. and Scott, G., Rubber Chem. Technol., 1984, vol. 57, p. 735.

    Google Scholar 

  5. Dolgina, L.K., Ovechkina, G.I., and Firsov, Yu.I., Abstracts of Papers, VI Vsesoyuznaya konferentsiya “Starenie i stabilizatsiya polimerov” (VIth All-Union Conf. “Aging and Stabilization of Polymers”), Ufa, 1983, p. 50.

  6. DePriest, J., Zheng, G.Y., Woods, S., Rilltma, D.P., Mikirova, N.A., and Zandle, M.E., Inorg. Chim. Acta, 1997, vol. 264, nos.1–2, p. 287.

    Google Scholar 

  7. Carrical, S., Doucette, S., Jones, C., Nazzaccol, C.I., and Halpem, A.M., J. Photochem. Photobiol. A: Chem., 1996, vol. 99, no.1, p. 29.

    Google Scholar 

  8. Kozlov, N.S., Misenzhnikov, V.V., and Kozlov, G.N., Zh. Obshch. Khim., 1965, vol. 35, no.1, p. 134.

    Google Scholar 

  9. Kozlov, N.S. and Isaeva, R.K., Khim. Geterotsikl. Soedin., 1965, no. 3, p. 379.

  10. Kozlov, N.S., Misenzhnikov, V.V., and Gaisinovich, M.S., Khim. Geterotsikl. Soedin., 1965, no. 3, p. 467.

  11. Kozlov, N.G., Gusak, K.N., and Makhnach, S.A., Khim. Geterotsikl. Soedin., 1996, no. 7, p. 960.

  12. Kozlov, N.S., 5,6-Benzokhinoliny (5,6-Benzoquinolines), Minsk: Nauka i Tekhnika, 1970, p. 28.

    Google Scholar 

  13. Grachek, V.I. and Kozlov, N.S., Dokl. Akad. Nauk BSSR, 1981, vol. 25, no.11, p. 1001.

    Google Scholar 

  14. Kozlov, N.S., Cherepok, V.I., and Prishchepenko, V.M., Vesti Akad. Navuk BSSR, Ser. Khim. Navuk, 1976, no. 1, p. 112.

  15. Vorob’eva, R.T., Kopytina, M.V., and Rozhkova, N.G., Zh. Prikl. Spektrosk., 1968, vol. 9, no.5, p. 837.

    Google Scholar 

  16. Brown, Ch. and Sikkel, B.J., J. Chem. Soc., Perkin Trans. 1, 1982, no. 12, p. 3007.

  17. Kozlov, N.G., Basalaeva, L.I., and Tychinskaya, L.Yu., Zh. Org. Chem., 2000, vol. 36, no.9, p. 1399.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus

    V. I. Grachek

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  1. V. I. Grachek
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Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 11, 2004, pp. 1878–1883.

Original Russian Text Copyright © 2004 by Grachek.

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Grachek, V.I. Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene. Russ J Gen Chem 74, 1748–1753 (2004). https://doi.org/10.1007/s11176-005-0094-4

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  • DOI: https://doi.org/10.1007/s11176-005-0094-4

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