Abstract
2,5-Disubstituted 3H-1,3,4-benzotriazepines were synthesized by heating of N-imidoyltetrazoles in toluene at 110°C. Alkylation of these compounds, as well as of 3H-pyrido[6,7-b][1,3,4]triazepines with alkyl halides in THF in the presence of potassium tert-butoxide gave the corresponding 1-alkyl derivatives in good yield and with high regioselectivity.
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REFERENCES
Myznikov, L.V., Esikov, K.A., Artamonova, T.V., and Koldobskii, G.I., Russ. J. Org. Chem., 2003, vol. 39, p. 731.
Koldobskii, G.I. and Ivanova, S.E., Russ. J. Org. Chem., 1995, vol. 31, p. 1435.
Morgenstern, O., Pharmazie, 2000, vol. 55, p. 871.
Koldobskii, G.I., Nikonova, I.V., Zhivich, A.B., Ostrovskii, V.A., and Poplavskii, V.S., Zh. Obshch. Khim., 1992, vol. 62, p. 194.
Ivanova, S.E., Koldobskii, G.I., and Ostrovskii, V.A., Khim. Geterotsikl. Soedin., 1997, p. 907.
Koldobskii, G., Ivanova, S., Nikonova, I., and Zhivich, A., Acta Chem. Scand., 1994, vol. 48, p. 596.
Artamonova, T.V. and Koldobskii, G.I., Russ. J. Org. Chem., 1997, vol. 33, p. 1767.
Artamonova, T.V., Alam, L.V., and Koldobskii, G.I., Russ. J. Org. Chem., 2000, vol. 36, p. 1700.
Nikulin, V.V., Artamonova, T.V., and Koldobskii, G.I., Russ. J. Org. Chem., 2003, vol. 39, p. 611.
Sunder, S. and Peet, N.P., J. Org. Chem., 1977, vol. 42, p. 2551.
Boyd, G.V., Cobb, J., Lindley, P.F., Mitchell, J.C., and Nicolaou, G.A., J. Chem. Soc., Chem. Commun., 1987, p. 99.
Lindley, P.F., Boyd, G.V., and Nicolaou, G.A., Acta Crystallogr., Sect. C, 1990, vol. 46, p. 1693.
Fusco, R., Marchesini, A., and Sannicolo, F., J. Heterocycl. Chem., 1986, vol. 23, p. 1795.
Kempten, G. and Schiewald, E., J. Prakt. Chem.,1965, vol. 28, p. 169.
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Nikulin, V.V., Artamonova, T.V. & Koldobskii, G.I. Tetrazoles: XLVI. 3H-1,3,4-Benzo- and Pyrido[6,7-b][1,3,4]triazepines from 5-Aryltetrazoles. Synthesis and Chemical Properties. Russian Journal of Organic Chemistry 39, 1525–1529 (2003). https://doi.org/10.1023/B:RUJO.0000010575.49890.da
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DOI: https://doi.org/10.1023/B:RUJO.0000010575.49890.da