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The synthesis and extraction properties of new 2-(phosphorylalkyl)-and 2-(phosphorylalkenyl)-substituted 1,8- and 1,6-naphthyridines

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Chemistry of Heterocyclic Compounds Aims and scope

New 1,8- and 1,6-naphthyridines containing a phosphoryl group in the side chain were synthesized via Friedlӓnder reaction by combining the appropriate aminonicotinic aldehydes and phosphoryl ketones in alcohol medium in the presence of basic catalysts (pyrrolidine or KOH). A series of phosphoryl-substituted 1,8-naphthyridines effectively extracted uranium(VI) from neutral aqueous solutions containing lanthanide(III) into 1,2-dichloroethane.

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Notes

  1. The phenomenon of double magnetic nonequivalence in NMR spectra of systems containing a prochiral phosphorus atom was first reported by M. I. Kabachnik with coworkers.21

  2. Compound 1d with a furyl substituent was not studied due to its low stability.

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This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 14-03-00695-a).

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Georgy V. Bodrin, Anna G. Matveeva, Evgenii I. Goryunov, Margarita P. Pasechnik, Rinat R. Aysin, Evgeny D. Savin, Alexander S. Peregudov, Yulia V. Nelyubina & Valery K. Brel

  2. Institute of Solid State Physics, Russian Academy of Sciences, 2 Academician Ossipyan St., Chernogolovka, 142432, Moscow District, Russia

    Alexander N. Turanov

  3. Institute of Microelectronics Technology Problems and High Purity Materials, Russian Academy of Sciences, 6 Academician Ossipyan St., Chernogolovka, 142432, Moscow District, Russia

    Vasilii K. Karandashev

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  1. Georgy V. Bodrin
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  2. Anna G. Matveeva
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  3. Evgenii I. Goryunov
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  4. Margarita P. Pasechnik
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  8. Evgeny D. Savin
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Correspondence to Anna G. Matveeva.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 583–591

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Bodrin, G.V., Matveeva, A.G., Goryunov, E.I. et al. The synthesis and extraction properties of new 2-(phosphorylalkyl)-and 2-(phosphorylalkenyl)-substituted 1,8- and 1,6-naphthyridines. Chem Heterocycl Comp 52, 583–591 (2016). https://doi.org/10.1007/s10593-016-1936-1

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  • DOI: https://doi.org/10.1007/s10593-016-1936-1

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