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Russian Journal of General Chemistry

, Volume 89, Issue 5, pp 906–912 | Cite as

Synthesis, Structure, and Properties of Novel Enamine Containing Coumarin and Phosphonium Fragments

  • L. D. PopovEmail author
  • I. N. Scherbakov
  • S. A. Borodkin
  • Yu. V. Revinskii
  • E. A. Kazoyan
  • G. A. Shaginyan
  • A. R. Sarkisyan
  • Sh. A. Markaryan
Article
  • 8 Downloads

Abstract

Condensation of 4-hydroxy-3-formylcoumarin with 4-aminobenzyl(triphenyl)phosphonium bromide has led to the formation of a phosphonium salt existing in DMSO solution as a mixture of two enamine forms, Z and E, according to NMR spectroscopy and quantum-chemical simulations data. Basing on the obtained salt, the ML2 metal chelates of zinc(II), copper(II), and nickel(II) have been synthesized. Luminescence properties of the ligand and its complex with zinc have been studied.

Keywords

enamines 4-hydroxy-3-formylcoumarin zinc(II) metal chelates phosphonium salts magnetochemistry 

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References

  1. 1.
    Pugachev, M.V., Shtyrlin, N.V., Sysoeva, L.P., Nikitina, E.V., Abdullin, T.I., Iksanova, A.G., Ilaeva, A.A., Musin, R.Z., Berdnikov, E.A., and Shtyrlin, Y.G., Bioorg. Med. Chem., 2013, vol. 21, no. 14, p. 4388. doi  https://doi.org/10.1016/j.bmc.2013.04.051 CrossRefGoogle Scholar
  2. 2.
    Pugachev, M.V., Shtyrlin, N.V., Sapozhnikov, S.V., Sysoeva, L.P., Iksanova, A.G., Nikitina, E.V., Musin, R.Z., Lodochnikova, O.A., Berdnikov, E.A., and Shtyrlin, Y.G., Bioorg. Med. Chem., 2013, vol. 21, no. 23, p. 7330. doi  https://doi.org/10.1016/j.bmc.2013.09.056 CrossRefGoogle Scholar
  3. 3.
    Galkina, I.V., Aksunova, A.F., Bakhtiyarov, D.I., Shulaeva, M.P., Pozdeev, O.K., Egorova, S.N., Bakhtiyarova, Y.V., and Galkin, V.I., Phosphorus, Sulfur, Silicon, Relat. Elem, 2016, vol. 191, nos. 11–12, p. 1676. doi  https://doi.org/10.1080/10426507.2016.1227821 CrossRefGoogle Scholar
  4. 4.
    Galkina, I., Bakhtiyarova, Y., Andriyashin, V., Galkin, V., and Cherkasov, R., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, nos. 1–3, p. 15. doi  https://doi.org/10.1080/10426507.2012.740694 CrossRefGoogle Scholar
  5. 5.
    Kanazava, A., Ikeda, T., and Endo, T., Antimicrob. Agent. Chemother., 1994, vol. 38, no. 5, p. 945. doi  https://doi.org/10.1128/AAC.38.5.945 CrossRefGoogle Scholar
  6. 6.
    Popa A., Davidescu C.M., Trif, R., Ilia Gh., Iliescu, S., and Dehelean Gh., React. Funct. Polym, 2003, vol. 55, no. 2, p. 151. doi  https://doi.org/10.1016/S1381-5148(02)00224-9 CrossRefGoogle Scholar
  7. 7.
    Masayo, I., Tomoo, I., and Biyuuki, K., Japan Patent 2002308713, 2002.Google Scholar
  8. 8.
    Xue, Y., Xiao, H., and Zhang Yi., Int. J. Mol. Sci., 2015, vol. 16, no. 2, p. 3626. doi  https://doi.org/10.3390/ijms16023626 CrossRefGoogle Scholar
  9. 9.
    Modica-Napolitano, J.S. and Aprille, J.R., Adv. Drug Delivery Rev., 2001, vol. 49, nos. 1–2, p. 63. doi  https://doi.org/10.1016/S0169-409X(01)00125-9 CrossRefGoogle Scholar
  10. 10.
    Murphy, M.P., Biochim. Biophys. Acta, 2008, vol. 1777, nos. 7–8, p. 1028. doi  https://doi.org/10.1016/j.bbabio.2008.03.029 CrossRefGoogle Scholar
  11. 11.
    Porteous, C.M., Logan, A., Evans, C., Ledgerwood, E.C., Menon, D.K., Aigbirhio, F., Smith, R.A.J., and Murphy, M.P., Biochim. Biophys. Acta, 2010, vol. 1800, no. 9, p. 1009. doi  https://doi.org/10.1016/j.bbagen.2010.06.001 CrossRefGoogle Scholar
  12. 12.
    Le Trionnaire, S., Perry, A., Szczesny, B., Szabo, C., Winyard, P.G., Whatmore, J.L., Wood, M.E., and Whiteman, M., Med. Chem. Commun., 2014, vol. 5, no. 6, p. 728. doi  https://doi.org/10.1039/C3MD00323J CrossRefGoogle Scholar
  13. 13.
    Millard, M., Gallagher, J.D., Olenyuk, B.Z., and Neamat, N., J. Med. Chem., 2013, vol. 56, no. 22, p. 9170. doi  https://doi.org/10.1021/jm4012438 CrossRefGoogle Scholar
  14. 14.
    Chalmers, S., Caldwell, S.T., Quin, C., Prime, T.A., James, A.M., Cairns, A.G., Murphy, M.P., McCarron, J.G., and Hartley, R.C., J. Am. Chem. Soc., 2012, vol. 134, no. 2, p. 758. doi  https://doi.org/10.1021/ja2077922 CrossRefGoogle Scholar
  15. 15.
    Stoyanovsky, D.A., Jiang, J., Murphy, M.P., Epperly, M., Zhang, X., Li, S., Greenberger, J., Kagan, V., and Bayir, H., ACS Med. Chem. Lett, 2014, vol. 5, no. 12, p. 1304. doi  https://doi.org/10.1021/ml5003635 CrossRefGoogle Scholar
  16. 16.
    Zhang Ch., Xin, B., Xi, Zh., Zhang, B., Li, Zh., Zhang, H., Li, Zh., and Hao, J., ACS Sust. Chem. Eng., 2018, vol. 6, no. 1, p. 1468. doi  https://doi.org/10.1021/acssuschemeng.7b03954 CrossRefGoogle Scholar
  17. 17.
    Pozzi, G., Quici, S., and Fish, R.H., J. Fluorine Chem., 2008, vol. 129, no. 10, p. 920. doi  https://doi.org/10.1016/j.jfluchem.2008.06.001 CrossRefGoogle Scholar
  18. 18.
    Werner, T., Adv. Synth. Catal., 2009, vol. 351, no. 10, p. 1469. doi  https://doi.org/10.1002/adsc.200900211 CrossRefGoogle Scholar
  19. 19.
    Mohamed, N.R., Halim, M.M.A., Gad, W.A., Zaid, M.F., Phosphorus, Sulfur, Silicon, Relat. Elem., 2007, vol. 182, no. 3, p. 551. doi  https://doi.org/10.1080/10426500600977379 CrossRefGoogle Scholar
  20. 20.
    Greenhill, J.V., Chem. Soc. Rev., 1977, vol. 6, p. 277. doi  https://doi.org/10.1039/CS9770600277 CrossRefGoogle Scholar
  21. 21.
    Lue, P. and Greenhill, J.V., Adv. Heterocycl. Chem., 1996, no. 67, p. 207. doi  https://doi.org/10.1016/S0065-2725(08)60072-0
  22. 22.
    Seo, K.D., Song, H.M., Lee, M.J., Pastore, M., Anselmi, C., De Angelis, F., Nazeeruddin, M.K., Graetzel, M., and Kim, H.K., Dyes Pigments, 2011, vol. 90, no. 3, p. 304. doi  https://doi.org/10.1016/j.dyepig.2011.01.009 CrossRefGoogle Scholar
  23. 23.
    Traven’, V.F., Ivanov, I.V., Panov, A.V., Safronova, O.B., and Chibisova, T.A., Russ. Chem. Bull., 2008, vol. 57, no. 9, p. 1989. doi  https://doi.org/10.1007/s11172-008-0267-5 CrossRefGoogle Scholar
  24. 24.
    Bagihalli, G.B., Avaji, P.G., Badami, P.S., and Patil, S.A., J. Coord. Chem., 2008, vol. 61, no. 17, p. 2793. doi  https://doi.org/10.1080/00958970801975109 CrossRefGoogle Scholar
  25. 25.
    Yan, M.-h., Li, T.-r., Yang, Z.-y., Inorg. Chem. Commun., 2011, vol. 14, no. 3, p. 463. doi  https://doi.org/10.10316/j.inoche.2010.12.027 CrossRefGoogle Scholar
  26. 26.
    An, J.-m., Yang, Z.-y., Yan, M.-h., and Li, T.-r., J. Luminescence, 2013, vol. 139, p. 79. doi  https://doi.org/10.10316/j.jlumin.2013.02.019 CrossRefGoogle Scholar
  27. 27.
    Xie, L., Chen, Y., Wu, W., Guo, H., Zhao, J., and Yu, X., Dyes Pigments, 2012, vol. 92, no. 3, p. 1361. doi  https://doi.org/10.1016/j.dyepig.2011.09.023 CrossRefGoogle Scholar
  28. 28.
    Kulkarni, A.D., Bagihalli, G.B., Patil, S.A., and Badami, P.S., J. Coord. Chem., 2009, vol. 21, no. 18, p. 3060. doi  https://doi.org/10.1080/00958970902914569 CrossRefGoogle Scholar
  29. 29.
    Chen, F., Liu, G., Shi, Y., Xi, P., Cheng, J., Hong, J., Shen, R., Yao, X., Bai, D., and Zeng, Z., Talanta, 2014, vol. 124, p. 139. doi  https://doi.org/10.1016/j.talanta.2014.02.034 CrossRefGoogle Scholar
  30. 30.
    Shkumat, A.P. and Berezhnoi, A.Yu., Vestn. Kharkov. Nats. Univ., 2008, no. 16 (39), p. 246.Google Scholar
  31. 31.
    Popov, L.D., Borodkin, S.A., Scherbakov, I.N., Tkachenko, Yu.N., Aleksandrov, G.G., Beloborodov, S.S., Zubenko, A.A., Kogan, V.A., and Maevskii, O.V., Russ. J.Gen. Chem., 2013, vol. 83, no. 7, p. 1376. doi  https://doi.org/10.1134/S107036321307013X CrossRefGoogle Scholar
  32. 32.
    Popov, L.D., Borodkin, S.A., Scherbakov, I.N., and Tkachenko, Yu.N., Russ. J. Gen. Chem., 2008, vol. 78, no. 4, p. 567. doi  https://doi.org/10.1134/S1070363208040099 CrossRefGoogle Scholar
  33. 33.
    Borodkin, S.A., Popov, L.D., Tsaturyan, A., Milenković, M.R., Shcherbakov, I.N., and Lukov, V.V., Phosphorus, Sulfur, Silicon, Relat. Elem., 2018, vol. 193, no. 6, p. 375. doi  https://doi.org/10.1080/10426507.2018.1424159 CrossRefGoogle Scholar
  34. 34.
    Murray, R.D.H., Mendes, J., and Brown, S.A., The Natural Coumarins: Occurrence, Chemistry and Biochemistry, New York: Wiley, 1982, p. 702.Google Scholar
  35. 35.
    Shkumat, A.P., Vestn. Kharkov. Nats. Univ., 1999, no. 4 (27), p. 150.Google Scholar
  36. 36.
    Milevskii, B.G., Chibisova, T.A., Solov’eva, N.P., Anisimova, O.S., Lebedev, V.S., Ivanov, I.V., and Traven, V.F., Chem. Heterocycl. Compd., 2013, vol. 48, no. 12, p. 1781. doi  https://doi.org/10.1007/s10593-013-1209-1 CrossRefGoogle Scholar
  37. 37.
    Parker, C.A., Photoluminescence of Solutions, Amsterdam: Elsevier, 1968.Google Scholar
  38. 38.
    Becke, A.D., J. Chem. Phys, 1993, vol. 98, no. 7, p. 5648. doi  https://doi.org/10.1063/1.464913 CrossRefGoogle Scholar
  39. 39.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., G. Scalmani, V.B., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., A.F. Izmaylov, Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision, A.02., 2009.Google Scholar
  40. 40.
    Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, no. 8, p. 2999. doi  https://doi.org/10.1021/cr9904009 CrossRefGoogle Scholar
  41. 41.
    Le Corre, M., Hercouet, A., Le Stanc, Y., and Le Baron, H., Tetrahedron, 1985, vol. 41, no. 22, p. 5313. doi  https://doi.org/10.1016/S0040-4020(01)96783-3 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • L. D. Popov
    • 1
    Email author
  • I. N. Scherbakov
    • 1
  • S. A. Borodkin
    • 1
  • Yu. V. Revinskii
    • 2
  • E. A. Kazoyan
    • 3
  • G. A. Shaginyan
    • 3
  • A. R. Sarkisyan
    • 3
  • Sh. A. Markaryan
    • 3
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia
  3. 3.Yerevan State UniversityYerevanArmenia

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