Abstract
Previously unknown 1,4-dihydropyridines containing acetyl, amide, benzoyl, ester, and cyano groups together with a nitro group were synthesized with preparative yields by a two-component Hantzsch synthesis based on 2-nitro-1,3-diphenylpropenone and various enamines. The nitrodihydropyridines were aromatized with sodium nitrite in acetic acid. The quaternary salts of low-basicity pyridines were produced with dimethyl sulfate and methyl fluorosulfonate.
Similar content being viewed by others
REFERENCES
K. Agrawal, S. B. Tang, M. W. Wolowyk, and E. E. Knaus, Drug. Des. Deliv., 3, 297 (1988).
C. R. Ganellin, S. K. Hosseini, Y. S. Khalaf, W. Tertiuk, and J. M. Arrang, J. Med. Chem., 38, 3342 (1995).
P. Krippeit-Drews, S. Britsch, F. Lang, and G. Drews, Adv. Exp. Med. Biol., 426, 355 (1997).
C. Linde, C. Luffler, C. Kessler, and U. Quast, Arch. Pharmacol., 356, 467 (1997).
P. Krippeit-Drews, S. Britsch, F. Lang, and G. Drews, Biochem. Biophys. Res. Commun., 200, 860 (1994).
R. Shan and E. E. Knaus, Bioorg. Med. Chem. Lett., 2613 (1999).
G. Luijtelaar, D. Wiaderna, C. Elants, and W. Scheenen, Eur. J. Pharmacol., 406, 381 (2000).
C. Temple, G. A. Rener, W. R. Waud, and P. E. Noker, J. Med. Chem., 35, 3686 (1992).
RF Patent Application No. 96102779/04 (1996); Byull. Izobr., No. 14, 57 (1998).
FRG Patent Application No. 3724909 (1989); Ref. Zh. Khim., 24O135P (1989).
FRG Patent Application No. 3601196 (1987); Ref. Zh. Khim., 6O65P (1988).
FRG Patent Application No. 3716652 (1988); Ref. Zh. Khim., 4O36P (1990).
FRG Patent Application No. 3732380 (1989); Ref. Zh. Khim., 3O44P (1990).
G. P. Shkil, V. Lusis, D. Muceniece, and R. S. Sagitullin, Tetrahedron, 51, 8599 (1995).
G. P. Shkil, L. V. Berdovich, V. Lusis, D. Muceniece, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., 86 (1995).
P. B. Terent′ev and A. P. Stankyavichyus, Mass-Spectrometric Analysis of Biologically Active Nitrogen Bases [in Russian], Mokslas, Vilnius (1987), p. 105.
L. Zalukaev, Izv. Akad. Nauk LatvSSR, 3, 107 (1953).
A. Dornow, A. Müller, and S. Lüpfert, Liebigs Ann., 594, 191 (1955).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sagitullina, G.P., Glizdinskaya, L.V., Sitnikov, G.V. et al. Nitropyridines. 1. Hantzsch Synthesis of Nitropyridines and Their Quaternary Salts. Chemistry of Heterocyclic Compounds 38, 1336–1341 (2002). https://doi.org/10.1023/A:1022174325051
Issue Date:
DOI: https://doi.org/10.1023/A:1022174325051