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A study of naphthyridines

III. Synthesis of 4,4-diaryl-1,4-dihydro-2,3-benzo-1,8-naphthyridines

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Chemistry of Heterocyclic Compounds Aims and scope

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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Literature cited

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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

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