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α-Amino acetals containing a phosphonate or phosphine oxide group. Synthesis and reactions with resorcinols

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Abstract

New α-amino acetals containing a phosphonate or phosphine oxide group were synthesized by the Kabachnik-Fields reaction in the ternary system amino acetal-paraformaldehyde-dialkyl phosphonate (or dialkylphosphine oxide). Condensation of dialkyl (2,2-dimethoxyethylamino)methylphosphonates with resorcinol and its derivatives in ethanol in the presence of hydrochloric acid, apart from the corresponding 2,2-bis(polyhydroxyphenyl) ethylammonium salts, gave 2,5-bis(polyhydroxyphenyl)-1,4-bis[(dialkoxyphosphoryl)methyl]-piperazines. Dialkyl[(2,2-dimethoxyethylamino)methyl]phosphine oxides (Alk = C8H17, C10H21) did not react with resorcinol derivatives under similar conditions, and analogous ammonium salts were obtained by heating the reactants in boiling trifluoroacetic acid.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    L. I. Vagapova, A. R. Burilov, Yu. K. Voronina, V. V. Syakaev, D. R. Sharafutdinova, I. Kh. Rizvanov & M. A. Pudovik

  2. Kazan National Research Technological University, ul. Karla Marksa 68, Kazan, 420015, Tatarstan, Russia

    L. R. Amirova & E. Yu. Pavlova

  3. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    A. R. Garifzyanov

Authors
  1. L. I. Vagapova
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  2. L. R. Amirova
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  3. E. Yu. Pavlova
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  4. A. R. Burilov
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  5. Yu. K. Voronina
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  6. V. V. Syakaev
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  7. D. R. Sharafutdinova
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  8. I. Kh. Rizvanov
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  9. A. R. Garifzyanov
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  10. M. A. Pudovik
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Correspondence to L. I. Vagapova.

Additional information

Original Russian Text © L.I. Vagapova, L.R. Amirova, E.Yu. Pavlova, A.R. Burilov, Yu.K. Voronina, V.V. Syakaev, D.R. Sharafutdinova, I.Kh. Rizvanov, A.R. Garifzyanov, M.A. Pudovik, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 484–491.

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Vagapova, L.I., Amirova, L.R., Pavlova, E.Y. et al. α-Amino acetals containing a phosphonate or phosphine oxide group. Synthesis and reactions with resorcinols. Russ J Org Chem 50, 469–477 (2014). https://doi.org/10.1134/S1070428014040034

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  • DOI: https://doi.org/10.1134/S1070428014040034

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