Abstract
4,4-Diaryl-1,4-dihydro-2,3-benzo-1,8-naphthyridines have been synthesized by the cyclization of diaryl 2-arylaminopyridin-3-yl carbinols. The latter were obtained by the reaction of methyl 2-arylaminonicotinates with arylmagnesium halides. With acid chlorides, the 4,4-diaryl-1, 4-dihydro-2,3-benzo-1,8-naphthyridines form 1-acyl derivatives. The pKa values of the 4,4-diaryl-1,4-dihydro-2,3-benzo-1,8-naphthyridines in nitrobenzene have been determined, and a correlation has been found of the pK a values with the σ * constants of the substituents (r=0.955, ϱ *= −1.53, pK ° a calc=2.51, s=0.01).
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M. E. Konshin and V. A. Khaldeeva, Khim. Geterotsikl. Soedin., 1393 (1973).
A. Baeyer and V. Villiger, Ber., 37, 3191 (1904).
M. E. Konshin and P. A. Petyunin, Zh. Obshch. Khim., 34, 3429 (1964).
R. W. Taft, in: Steric Effects in Organic Chemistry, edited by M. S. Newman, Wiley (1956).
A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, 1st ed., Methuen, London (1962).
V. P. Chesnokov and M. E. Konshin, Izv. Vysshykh Uchebn. Zaved., Ser. Khim. (1974) (in press).
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For Communication II, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 119–121, January, 1974.
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Konshin, M.E., Chesnokov, V.P. A study of naphthyridines. Chem Heterocycl Compd 10, 105–107 (1974). https://doi.org/10.1007/BF00475922
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DOI: https://doi.org/10.1007/BF00475922