Abstract
The synthetic route to 4-substituted bisnaphthalimides consisting in reaction of 4-halonaphthalic anhydrides with a,w-diaminoalkanes followed by halogen substitution with dialkylamino group is more promising than imidating coupling of 4-dialkylaminonaphthalic anhydrides for it opens wider synthetic opportunities and ensures better yields of target products. Dihalosubstituted bis-naphthalimides can be prepared by N-alkylation of the corresponding naphthalimides with polymethylene dibromides under conditions of phase-transfer catalysis in the presence of tetraalkylammonium salts.
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REFERENCES
El-Naggar, A.M., Zaher, M.R., and Salem, A.A., Egypt. J. Chem., 1982, vol. 25, p. 445.
El-Naggar, A.M., Zaher, M.R., and Salem, A.A., Ind. J. Chem., 1982, vol. 21B, p. 1106.
Camacho, M.A., Torres, A.I., Gil, M.E., and Obregon, M.M., Ruz, V., Arzneim.-Forsch. Drug, Res., 1994, vol. 44, p. 659.
Gancedo, A.G., Gil-Fernandez, C., Vilas, P., Perez, S., Rodriguez, F., Paez, E., Brana, M.F., and Roldan, C.M., Antiviral Res., 1984, vol. 4, p. 201.
Chang, S.C., Archer, B.J., Utecht, R.E., Lewis, D.E., Judy, M.M., and Matthews, J.L., Bioorg. Med. Chem. Let., 1993, vol. 3, p. 555.
Brana, M.F., Castellano, J.M., Moran, M., Perez de Vega, M.J., Romerdahl, C.A., Qian, X.D., Bousquet, P., Emling, F., Schlick, E., and Keilhauer, G., Anti-Cancer Drug Design, 1993, vol. 8, p. 257.
Brana, M.F., Castellano, J.M., Moran, M., Perez de Vega, M.J., Qian, X.D., Romerdahl, C.A., and Keilhauer, G., Eur. J. Med. Chem., 1995, vol. 30, p. 235.
Krasovitskii, B.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores), Moscow: Khimiya, 1984, p. 156.
Shevchenko, E.A., Distanov, V.B., and Blank, F.B., Zav. Lab., 1984, vol. 50, p. 5.
Malkes, L. Ya., Minakova, R.A., and Bedrik, A.I., Zh. Prikl. Spektr., 1991, vol. 55, p. 820.
Utsugi, K. and Takano, S., J. Electrochem. Soc., 1992, vol. 139, p. 3610.
Krasovitskii, B.M., Shevchenko, E.A., and Distanov, V.B., Zh. Org. Khim., 1983, vol. 19, p. 1305.
Krasovitskii, B.M., Shevchenko, E.A., Lyubarskaya, A.G., Kuznetsov, A.M., Slezko, G.F., Mikulenko, V.V., and Seleznev, M.M., USSR Patent 326209, 1972; SSSR Ref. Zh. Khim., 1972, vol. 18N, p. 142P.
Anikin, V.F. and Kupriyan, D.G., Zh. Or. Khim., 2000, vol. 36, p. 1720.
Alexiou, S.A., Tychopoulos, V., Ghorbanian, S., Tyman, J.H.P., Brown, R.G., and Brittain, P.I., J. Chem. Soc., Perkin, Trans. 2, 1990, vol. 5, p. 837.
Anikin, V.F., Krasnova, E.A., and Kupriyan, D.G., Zh. Prikl. Khim., 2000, vol. 73, p. 459.
Laboratorni Technika Organicki Chemie, Keil, B., Ed., Prague: Nakladatelstvi Cheskoslovenski Akademie Ved, 1963.
Dziewonski, K. and Zakrzewska-Baranowska, M., Bull. Intern. Acad. Polon., 1927, p. 65.
Petrenko, G.P. and Tel'nyuk, E.N., Zh. Org. Khim., 1966, vol. 2, p. 722.
Jones, L.A., Joyner, C.T., Kim, H.K., and Kyff, R.A., Canad. J. Chem., 1970, vol. 48, p. 3132.
Karishin, A.P. and Kustol, D.M., Zh. Org. Khim., 1958, vol. 28, p. 692.
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Kupriyan, D.G., Anikin, V.F., Merz, A. et al. Synthesis of 4-Substituted Bisnaphthalimides. Russian Journal of Organic Chemistry 40, 699–704 (2004). https://doi.org/10.1023/B:RUJO.0000043717.08167.c6
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DOI: https://doi.org/10.1023/B:RUJO.0000043717.08167.c6