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Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles

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Abstract

A primary functionalization of quinolines polyfluorinated at the benzene ring (5,7-difluoro-, 5,7,8-trifluoro-, 5,6,8-trifluoro-, 8-chloro-5,7-difluoro-, 5,6,7,8-tetrafluoro-, and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines) by the reaction with nitrogen-centered nucleophiles (aqueous and liquid ammonia, hydrazine hydrate, piperidine) has been studied. If the molecule of fluorinated quinoline contains three or four halogen atoms, their combined orientation effect outweighs the influence of the heterocycle N atom. It was found that the orientation of substitution in the reactions of 5,6,8-trifluoro- and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines with piperidine depends on temperature, because the enthalpy control of the ratio of the rates of competing reactions changes to the entropy control. Nineteen new quinoline derivatives containing F atoms and amino or modified amino groups in the benzene ring have been obtained.

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Authors and Affiliations

  1. N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    L. Yu. Safina, G. A. Selivanova, I. Yu. Bagryanskaya & V. D. Shteingarts

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    V. D. Shteingarts

Authors
  1. L. Yu. Safina
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  2. G. A. Selivanova
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  3. I. Yu. Bagryanskaya
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  4. V. D. Shteingarts
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Correspondence to V. D. Shteingarts.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1022–1033, May, 2009.

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Safina, L.Y., Selivanova, G.A., Bagryanskaya, I.Y. et al. Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles. Russ Chem Bull 58, 1049–1061 (2009). https://doi.org/10.1007/s11172-009-0134-z

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  • DOI: https://doi.org/10.1007/s11172-009-0134-z

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