Abstract
4-Pyridyl-2,3-dihydro-1H-1,5-benzodiazepin-2-ones were obtained by the condensation of ethyl nicotinoyl- or isonicotinoylacetates with o-phenylenediamine. Alkylation of the pyridylbenzodiazepinones with ethyl iodide under phase-transfer catalysis conditions occurred at the amide nitrogen of the heterocycle, whereas in nitromethane it occurred at the nitrogen of the pyridine substituent. Bromination with N-bromosuccinimide occurred at position 3 of the heterocycle. Pyridyldibenzodiazepinones underwent thermal rearrangement to derivatives of vinylbenzimidazole.
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REFERENCES
M. D. Mashkovskii, Medicinal Substances [in Russian], Torsing, Krar'kov (1998).
R. Barchet and K. W. Merz, Tetrahedron. Lett., 2239 (1964).
V. D. Orlov, N. N. Kolos, and B. M. Zolotarev, Khim. Geterotsikl. Soedin., 390 (1983).
G. Vernin, H. Domloj, C. Siv, J. Motzger, A. Archavlis, and J. R. Llinas, Chemica Scripta, 157 (1980).
A. F. Pozharskii, Theoretical Bases of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
F. Malik, M. Hassan, D. Rosenbaum, and H. Duddek, Magn. Reson. Chem., 27, 391 (1989).
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Bozhanov, V.I., Ivonin, S.P. Synthesis of 4-Pyridyl-2,3-dihydro-1H-1,5-benzodiazepin-2-ones. Chemistry of Heterocyclic Compounds 38, 1098–1103 (2002). https://doi.org/10.1023/A:1021213517045
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DOI: https://doi.org/10.1023/A:1021213517045