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

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• 作者：L. I. Vagapova (1)
  L. R. Amirova (2)
  E. Yu. Pavlova (2)
  A. R. Burilov (1)
  Yu. K. Voronina (1)
  V. V. Syakaev (1)
  D. R. Sharafutdinova (1)
  I. Kh. Rizvanov (1)
  A. R. Garifzyanov (3)
  M. A. Pudovik (1)
  
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 2014
• 年：2014
• 卷：50
• 期：4
• 页码：469-477
• 全文大小：
• 参考文献：1. Granik, V.G., Zhidkova, A.M., and Glushkov, R.G., / Usp. Khim., 1977, vol. 46, p. 685. CrossRef
  2. Chien, T.C., Meade, E.A., Hinkley, J.M., and Townsed, L.B., / Org. Lett., 2004, vol. 6, p. 2857; Pandit, C.R., Polniaszek, R.P., and Thottathil, J.K., / Synth. Commun., 2002, vol. 32, p. 2427; Graulich, A. and Li茅geois, J.F., / Synthesis, 2004, no. 12, p. 1935. CrossRef
  3. Klumpp, D.A., Sanchez, G.V., Jr., Aguirre, S.L., Zhang, Y., and de Leon, S., / J. Org. Chem., 2002, vol. 67, p. 5028; Plazuk, D. and Zakrzewski, J., / Phosphorus, Sulfur Silicon Relat. Elem., 2005, vol. 180, p. 2709. CrossRef
  4. Burilov, A.R., Gazizov, A.S., Pudovik, M.A., and Konovalov, A.I., / Russ. J. Gen. Chem., 2007, vol. 77, p. 98. CrossRef
  5. Burilov, A.R., Knyazeva, I.R., Sadykova, Yu.M., Pudovik, M.A., Habicher, W.D., Baier, I., and Konovalov, A.I., / Russ. Chem. Bull., Int. Ed., 2007, vol. 56, p. 1144. CrossRef
  6. Burilov, A.R., Gazizov, A.S., Kharitonova, N.I., Pudovik, M.A., Habicher, W.D., Baier, I., and Konovalov, A.I., / Russ. Chem. Bull., Int. Ed., 2007, vol. 56, p. 330; Burilov, A.R., Gazizov, A.S., Kharitonova, N.I., Pudovik, M.A., and Konovalov, A.I., / Russ. J. Gen. Chem., 2007, vol. 77, p. 487; Knyazeva, I.R., Burilov, A.R., and Pudovik, M.A., / Russ. Chem. Bull., Int. Ed., 2011, vol. 60, p. 1956. CrossRef
  7. Vagapova, L.I., Burilov, A.R., Pudovik, M.A., Habicher, W.D., Syakaev, V.V., and Konovalov, A.I., / Mendeleev Commun., 2011, vol. 21, p. 44. CrossRef
  8. Khakimov, M.S., Gazizov, A.S., Burilov, A.R., Pudovik, M.A., and Konovalov, A.I., / Russ. J. Gen. Chem., 2009, vol. 79, p. 1163. CrossRef
  9. Stoikov, I.I., Repejkov, S.A., Antipin, I.S., and Konovalov, A.I., / Heteroatom Chem., 2000, vol. 11, p. 518; Cherkasov, R.A., Garifzyanov, A.R., Bazanova, E.B., Davletshin, R.R., and Leont鈥檈va, S.V., / Russ. J. Gen. Chem., 2012, vol. 82, p. 33. CrossRef
  10. Cherkasov, R.A., Garifzyanov, A.R., Galleev, R.R., Kurnosova, N.V., Davletshin, R.R., and Zakharov, S.V., / Russ. J. Gen. Chem., 2011, vol. 81, p. 1464. CrossRef
  11. Mastryukova, T.A., Artyushin, O.I., Odinets, I.L., and Tananaev, I.G., / Ross. Khim. Zh., 2005, vol. 49, no. 2, p. 86.
  12. Wichmann, O., Sillanpaa, R., and Lehtonen, A., / Coord. Chem. Rev., 2012, vol. 256, p. 371. CrossRef
  13. Donkor, I.O., Huang, T.L., Tao, B., Rattendi, D., Lane, S., Vargas, M., Goldberg, B., and Bacchi, C., / J. Med. Chem., 2003, vol. 46, p. 1041; Vanden Eynde, J.J., Mayence, A., LeCour, L., Jr., and Huang, T.L., / Med. Chem. Res., 2003, vol. 12, p. 401. CrossRef
  14. Sheldrick, G.M., / Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112. CrossRef
  15. Sheldrick, G.M., / SHELXL-97. Program for Crystal Structure Refinement, G枚ttingen, Germany: Univ. of G枚ttingen, 1997.
  16. Farrugia, L.J., / J. Appl. Crystallogr., 1999, vol. 32, p. 837. CrossRef
  17. / APEX (Version 2.1), SAINTPlus. Data Reduction and Correction Program. Version 7.31A, Bruker Advanced X-Ray Solutsions, Madison, Wisconsin, USA: Bruker AXS, 2006.
  18. Spek, A.L., / Acta Crystallogr., Sect. A, 1990, vol. 46, p. 34.
  19. Vagapova, L.I., Fahertdinova, A.F., Burilov, A.R., and Pudovik, M.A., / Mendeleev Commun., 2012, vol. 22, no. 6, p. 325. CrossRef
  20. Vagapova, L.I., Pavlova, E.Yu., and Burilov, A.R., / Vestn. Kazan. Gos. Tekh. Univ., 2013, vol. 17, no. 4, p. 56.
  
• 作者单位：L. I. Vagapova (1)
  L. R. Amirova (2)
  E. Yu. Pavlova (2)
  A. R. Burilov (1)
  Yu. K. Voronina (1)
  V. V. Syakaev (1)
  D. R. Sharafutdinova (1)
  I. Kh. Rizvanov (1)
  A. R. Garifzyanov (3)
  M. A. Pudovik (1)
  
  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia
  2. Kazan National Research Technological University, ul. Karla Marksa 68, Kazan, 420015, Tatarstan, Russia
  3. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia
  
• ISSN：1608-3393

文摘

New 伪-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.