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Effect of the basicity of the aza group on the direction of nucleophilic substitution reactions in imidazo[4, 5-f]quinolines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The quinoline ring in imidazo[4,5-f]quinolines is more reactive than the imidazole ring with respect to nucleophiles (phenyllithium and sodium amide). An assumption, which is confirmed by molecular orbital calculations and the pKa values, is expressed that the direction of the corresponding reactions is primarily determined by the relative basicity of the aza groups (the nucleophile attacks the C atom next to the more basic nitrogen atom) and not by the magnitude of the positive charge or the energy of anionic localization on the C2 and C7 atoms in the neutral molecule.

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Authors and Affiliations

  1. Rostov-on-Don State University, USSR

    B. I. Khristich, V. A. Kruchinin, A. F. Pozharskii & A. M. Simonov

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  1. B. I. Khristich
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  2. V. A. Kruchinin
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  3. A. F. Pozharskii
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  4. A. M. Simonov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 814–817, June, 1971.

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Khristich, B.I., Kruchinin, V.A., Pozharskii, A.F. et al. Effect of the basicity of the aza group on the direction of nucleophilic substitution reactions in imidazo[4, 5-f]quinolines. Chem Heterocycl Compd 7, 759–762 (1971). https://doi.org/10.1007/BF00476828

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  • DOI: https://doi.org/10.1007/BF00476828

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