Russian Journal of General Chemistry

, Volume 87, Issue 12, pp 2895–2897 | Cite as

Addition of Diphenylphosphine to Two Molecules of 1,4-Naphthoquinone

  • N. R. Khasyatullina
  • A. M. Vazykhova
  • V. F. Mironov
Letters to the Editor
  • 4 Downloads

Abstract

According to NMR data, diphenylphosphine reacted with two equivalents of 1,4-naphthoquinone under mild conditions to form betaine, 1',4'-dihydroxynaphth-2'-yl-diphenylphosphonium (1-hydroxynaphth-2-yl-4-ate), which was converted to bis(1,4-dihydroxynaphth-2-yl)diphenylphosphonium salts when treated with hydrogen bromide or trifluoracetic acid.

Keywords

secondary phosphine zwitterion phosphonium salt 1,4-naphthoquinone 

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References

  1. 1.
    Millard, M., Pathania, D., Shabaik, Y., Taheri, L., Deng, J., and Neamati, N., PLoS ONE, 2010, vol. 5, p. 1. doi 10.1371/journal.pone.0013131CrossRefGoogle Scholar
  2. 2.
    Kagan, V.E., Wipf, P., Stoyanovsky, D., Greenberger, J.S., Borisenko, G., Belikova, N.A., Yanamala, N., Samhan Arias, A.K., Tungekar, M.A., Jiang, J., Tyurina, Y.Y., Ji, J., Klein-Seetharaman, J., Pitt, B.R., Shvedova, A.A., and Bayir, H., Adv. Drug Deliv. Rev., 2009, vol. 61, no. 14, p. 1375. doi 10.1016/j.addr.2009. 06.008CrossRefGoogle Scholar
  3. 3.
    Wu, T., Xie, A.-G., Tan, S.-Z., and Cai, X., Colloids and Surfaces (B), 2011, vol. 86, p. 232. doi 10.1016/j.colsurfb.2011.04.009CrossRefGoogle Scholar
  4. 4.
    Khasiyatullina, N.R., Mironov, V.F., Bogdanov, A.V., Zobov, V.V., Voloshina, A.D., Kulik, N.V., and Konovalov, A.I., Pharm. Chem. J., 2009, vol. 43, no. 11, p. 610. doi 0091-150X/09/4311-0610CrossRefGoogle Scholar
  5. 5.
    Strobykina, I.Yu., Belenok, M.G., Semenova, M.N., Semenov, V.V., Babaev, V.M., Rizvanov, I.Kh., Mironov, V.F., and Kataev, V.E., J. Nat. Prod., 2015, vol. 78, p. 1300. doi 10.1021/acs.jnatprod.5b00124CrossRefGoogle Scholar
  6. 6.
    Biasutto, L., Mattarei, A., Sassi, N., Azzolini, M., Romio, M., Paradisi, C., and Zoratti, M., Anti-Cancer Agents in Med. Chem., 2014, vol. 14, no. 10, p. 1332. doi 10.2174/1871520614666140627150054CrossRefGoogle Scholar
  7. 7.
    Jara, J.A., Castro-Castillo, V., Saavedra-Olavarría, J., Peredo, L., Pavanni, M., JaCa, F., Letelier, M.E., Parra, E., Becker, M.I., Morello, A., Kemmerling, U., Maya, J.D., and Ferreira, J., J. Med. Chem., 2014, vol. 57, no. 6, p. 2440. doi 10.1021/jm500174vCrossRefGoogle Scholar
  8. 8.
    Chakraborty, A. and Jana, N.R., J. Phys. Chem. (C), 2015, vol. 119, no. 5, p. 2888. doi 10.1021/jp511870eGoogle Scholar
  9. 9.
    Li, Z., Lopez, M., Hardy, M.I., McAllister, D.M., Kalyanaraman, B., and Zhao, M., Cancer Biother. Radiopharm., 2009, vol. 24, no. 5, p. 579. doi 10.1089/cbr.2008.0606CrossRefGoogle Scholar
  10. 10.
    Allen, D.W. and Tebby, J.S., Organophosphorus Chem., 2001, vol. 33. doi 10.1039/9781847554529CrossRefGoogle Scholar
  11. 11.
    Arisawa, M. and Yamaguchi, M., ACS Symposium Series, 2009, vol. 965, no. 22, p. 477. doi 10.1021/bk-2007-0965.ch022Google Scholar
  12. 12.
    Beletskaya, I.P. and Kazankova, M.A., Russ. J. Org. Chem., 2002, vol. 38, no. 10, p. 1391. doi 10.1023/A:1022685801622CrossRefGoogle Scholar
  13. 13.
    Khasiyatullina, N.R. and Mironov, V.F., Russ. J. Org. Chem., 2015, vol. 51, no. 9, p. 1343. doi 10.1134/S1070428015090225CrossRefGoogle Scholar
  14. 14.
    Mironov, V.F., Khasiyatullina, N.R., and Krivolapov, D.B., Tetrahedron Lett., 2015, vol. 56, no. 51, p. 7132. doi 10.1016/j.tetlet.2015.11.039CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • N. R. Khasyatullina
    • 1
  • A. M. Vazykhova
    • 1
  • V. F. Mironov
    • 1
  1. 1.Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific CenterRussian Academy of SciencesKazan, TatarstanRussia

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