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Synthesis of aminobismethylenephosphonic acids on a platform of p-tert-Butylthiacalix[4]arene in 1,3-alternate configuration

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Abstract

Aminobismethylenephosphonic acids on a platform of p-tert-butylthiacalix[4]arene were obtained by reacting macrocyclic amines with phosphorous acid and formaldehyde under acid catalysis. Free phenol hydroxy groups on the lower rim of p-tert-butylthiacalix[4]arene were found to inhibit the interaction with the amino moieties of the macrocycle. In the case of amino derivatives of thiacalix[4]arene containing no hydroxy groups the reaction led to the formation of target compounds in good yields.

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References

  1. Babine, R.E. and Bender, S.L., Chem. Rev., 1997, vol. 97, no. 5, p. 1359. DOI: 0.1021/cr960370z.

    Article  CAS  Google Scholar 

  2. Kodadek, T., Chem. Biol., 2001, vol. 8, no. 2, p. 105. DOI: 10.1016/S1074-5521(00)90067-X.

    Article  CAS  Google Scholar 

  3. De, M., Ghosh, P.S., and Rotello, V.M., Adv. Mater., 2008, vol. 20, no. 22, p. 4225. DOI: 10.1002/adma.200703183.

    Article  CAS  Google Scholar 

  4. Cretich, M., Damin, F., Pirri, G., and Chiari, M., Biomol. Eng., 2006, vol. 23, nos. 2–3, p. 77. DOI: 10.1016/j.bioeng. 2006.02.001.

    Article  CAS  Google Scholar 

  5. Margulies, D. and Hamilton, A.D., Curr. Opin. Chem. Biol., 2010, vol. 14, no. 6, p. 705. DOI: 10.1016/j.cbpa.2010.07.017.

    Article  CAS  Google Scholar 

  6. Synthetic Receptors for Biomolecules: Design Principles and Applications, Smith, B., Ed., RSC Publishing, 2015, p. 362. DOI: 10.1039/9781782622062-00369.

  7. Chothia, C. and Janin, J., Nature, 1975, vol. 256, no. 5520, p. 705. DOI: 10.1038/256705a0.

    Article  CAS  Google Scholar 

  8. Kafarski, P. and Lejczak, B., Curr. Med. Chem., 2001, vol. 1, no. 3, p. 301. DOI: 10.2174/1568011013354543.

    CAS  Google Scholar 

  9. Hiratake, J. and Oda, J., Biosci. Biotechnol. Biochem., 1997, vol. 61, no. 2, p. 211. DOI: 10.1271/bbb.61.211.

    Article  CAS  Google Scholar 

  10. Beck, J., Gharbi, S., Herteg-Fernea, A., Vercheval, L., Bebrone, C., Lassaux, P., Zervosen, A., and Marchand-Brynaert, J., J. Org. Chem., 2009, vol. 1, p. 85. DOI: 10.1002/ejoc.200800812.

    Google Scholar 

  11. Antipin, I.S., Stoikov, I.I., Pinkhassik, E.M., Fitseva, N.A., Stibor, I., and Konovalov, A.I., Tetrahedron Lett., 1997, vol. 38, no. 33, p. 5865. DOI: 10.1016/S0040-4039(97) 01305-1.

    Article  CAS  Google Scholar 

  12. Stoikov, I.I., Repeikov, S.A., Antipin, I.S., and Konovalov, A.I., Heteroatom. Chem., 2000, vol. 11, no. 7, p. 518. DOI: 10.1002/1098-1071(2000) 11:7<518::AID-HC10>3.0.CO;2-#.

    Article  CAS  Google Scholar 

  13. Phosphorus: Properties, Health Effects and the Environment, Da-Xia Yang and Ming Yue Chen, Eds., New York: Nova Science Publ. Inc., 2012, p.1.

  14. Agafonova, M.N., Mostovaya, O.A., Antipin, I.S., Konovalov, A.I., and Stoikov, I.I., Mendeleev Commun., 2012, vol. 22, no. 2, p. 80. DOI: 10.1016/j.mencom.2012.03.009.

    Article  CAS  Google Scholar 

  15. Mostovaya, O.A., Agafonova, M.N., Galukhin, A.V., Khayrutdinov, B.I., Islamov, D., Kataeva, O.N., Antipin, I.S, Konovalov, A.I., and Stoikov, I.I., J. Phys. Org. Chem., 2014, vol. 27, no. 1, p. 57. DOI: 10.1002/poc.3236.

    Article  CAS  Google Scholar 

  16. Cherenok, S., Vovk, A., Muravyova, I., Shivanyuk, A., Kukhar, V., Lipkowski, J., and Kalchenko, V., Org. Lett., 2006, vol. 8, no. 4, p. 549. DOI: 10.1021/ol052469a.

    Article  CAS  Google Scholar 

  17. Shkrabak, O.A., Kalchenko, O.I., Rodik, R.V., Veklich, T.O., Kalchenko, V.I., and Kosterin, S.O., Ukr. Biochem. J., 2008, vol. 80, no. 2, p.90.

    CAS  Google Scholar 

  18. Moedritzer, K. and Irani, R.R., J. Org. Chem., 1966, vol. 31, no. 5, p. 1603. DOI: 10.1021/jo01343a067.

    Article  CAS  Google Scholar 

  19. Clearfield, A. and Demadis, K., Metal Phosphonate Chemistry: From Synthesis to Applications, RSC Publishing, 2012, vol. 6, p.179.

    Google Scholar 

  20. Galukhin, A.V., Zaikov, E.N., Antipin, I.S., Konovalov, A.I., and Stoikov, I.I., Macroheterocycles, 2012, vol. 5, no. 3, p. 266. DOI: 10.1016/j.mencom.2009.07.006.

    Article  CAS  Google Scholar 

  21. Liang, L., Wei-wei, G., and Chao-guo, Y., Chem. Res. Chinese Univ., 2010, vol. 26, no. 1, p. 38. DOI: 10.6060/mhc2012. 120781s.

    CAS  Google Scholar 

  22. Głowacki, Z., Hoffmann, M., Topolski, M., and Rachoń, J., Phosphorus, Sulfur, Silicon, Relat. Elem., 1991, vol. 60, nos. 1–2, p. 67. DOI: 10.1080/10426509108233926.

    Article  Google Scholar 

  23. Kormachev, V.V. and Fedoseev, M.S., Preparativnaya khimiya fosfora (Phosphorus Preparative Chemistry), Perm: Ural. Otd. Ross. Akad. Nauk, 1992, p. 5.

    Google Scholar 

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Authors and Affiliations

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

    K. S. Shibaeva, A. A. Nazarova, D. I. Kuznetsova & I. I. Stoikov

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  1. K. S. Shibaeva
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  2. A. A. Nazarova
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  3. D. I. Kuznetsova
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  4. I. I. Stoikov
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Correspondence to I. I. Stoikov.

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Original Russian Text © K.S. Shibaeva, A.A. Nazarova, D.I. Kuznetsova, I.I. Stoikov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3, pp. 437–441.

To the 100th Anniversary of A.N. Pudovik

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Shibaeva, K.S., Nazarova, A.A., Kuznetsova, D.I. et al. Synthesis of aminobismethylenephosphonic acids on a platform of p-tert-Butylthiacalix[4]arene in 1,3-alternate configuration. Russ J Gen Chem 86, 579–583 (2016). https://doi.org/10.1134/S1070363216030130

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  • DOI: https://doi.org/10.1134/S1070363216030130

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