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Directed synthesis of tertiary phosphine chalcogenides with pyridine and hydroxy functions

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Abstract

Secondary phosphine chalcogenides react with pyridine-2-, pyridine-3-, and pyridine-4-carbaldehydes under mild noncatalytic conditions (22–43°C, 1–8.5 h) to form in 81–98% yield functional tertiary phosphine chalcogenides containing pyridine and hydroxy functions.

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References

  1. McFarlane, C.H.E., McFarlane, W., and Muir, A.S., Polyhedron, 1990, vol. 9, no. 14, p. 1757.

    Article  CAS  Google Scholar 

  2. Casares, A., Coco, S., Espinet, P., and Lin, Y.-S., Organometallics, 1995, vol. 14, p. 3058.

    Article  CAS  Google Scholar 

  3. Chelucci, G., Cabras, M.A., Botteghi, C., Basoli, C., and Marchetti, M., Tetrahedron Asymm., 1996, vol. 7, no. 3, p. 885.

    Article  CAS  Google Scholar 

  4. Espinet, P., Hernando, R., Iturbe, G., Villafane, F., Orpen, A.G., and Pascual, I., Eur. J. Inorg. Chem., 2000, p. 1031.

  5. Casares, J.A., Espinet, P., Martın-Alvarez, J.M., Espino, G., Perez-Manrique, M., and Vattier, F., Eur. J. Inorg. Chem., 2001, p. 289.

  6. Graiff, C., Ienco, A., Massera, C., Mealli, C., Predieri, G., Tiripicchio, A., and Ugozzoli, F., Inorg. Chim. Acta, 2002, vol. 330, p. 95.

    Article  CAS  Google Scholar 

  7. Kling, C., Ott, H., Schwab, G., and Stalke, D., Organometallics, 2008, vol. 27, p. 5038.

    Article  CAS  Google Scholar 

  8. Pai, Z.P., Berdnikova, P.V., Tolstikov, A.G., Roor, O.N., Khlebnikova, T.B., Gusarova, N.K., Malysheva, S.F., Ivanova, N.I., and Trofimov, B.A., React. Kinet. Catal. Lett., 2008, vol. 94, no. 2, p. 319.

    Article  CAS  Google Scholar 

  9. Borner, A., Phosphorus Ligands in Asymmetric Catalysis Synthesis an,d Applications, Weinheim: Wiley-VCH Verlag, 2008.

    Google Scholar 

  10. Saucedo, A.S.A., Hagenbach, A., and Abram, U., Inorg. Chem. Comm., 2009, vol. 12, p. 128.

    Article  Google Scholar 

  11. Gusarova N.K., Kuznetsova, E.E., Arbuzova, S.N., Shaikhudinova, S.I., Malysheva, S.F., Kozlova, G.V., Zorina, E.F., and Trofimov, B.A., Pharm. Chem. J., 1994, vol. 28, no. 9, p. 654.

    Article  Google Scholar 

  12. Gusarova, N.K., Kuznetsova, E.E., Shaikhudinova, S.I., Dmitriev, V.I., Malysheva, S.F., Kozlova, G.V., and Trofimov, B.A., Pharm. Chem. J., 1996, vol. 30, no. 7, p. 463.

    Article  Google Scholar 

  13. Mahepal, S., Bowen, R., Mamo, M.A., Layh, M., and van Rensburg, C.E.J., Metal-Based Drugs, 2008, vol. 2008, p. 1.

    Article  Google Scholar 

  14. Liu, J.J., Galettis, P., Farr, A., Mahara, L., Samarasinha, H., McGechan, A.C., Baguley, B.C., Bowen, R.J., Berners-Price, S.J., and McKeage, M.J., J. Inorg. Biochem., 2008, vol. 102, p. 303.

    Article  CAS  Google Scholar 

  15. Malysheva S.F., Doctoral (Chem.) Dissertation, Irkutsk, 2001.

  16. Uchida, Y., Onoue, K., Tada, N., and Nagao, F., Tetrahedron Lett., 1989, vo1. 30, no. 5, p. 567.

    Article  CAS  Google Scholar 

  17. Trofimov, B.A., Andriyankova, L.V., Shaikhudinova, S.I., Kazantseva, T.I., Mal’kina, A.G., Zhivet’ev, S.A., and Afonin, A.V., Synthesis, 2002, no. 7, p. 853.

  18. Uchida, Y., Matsumoto, M., and Kawamura, H., Heteroatom. Chem., 2003, vol. 14, no. 1, p. 72.

    Article  CAS  Google Scholar 

  19. Gusarova, N.K., Ivanova, N.I., Volkov, P.A., and Larina, L.I., Synthesis, 2008, no. 21, p. 3523.

  20. Herd, O., Heβler, A., Hingst, M., Machnitzki, P., Terrer, M., Stelzer, O., Catalysis Today, 1998, vol. 42, p. 413.

    Article  CAS  Google Scholar 

  21. Chow, H.-F., Mong, T.K.-K., Nongrum, M.F., and Wan, C.-W., Tetrahedron, 1998, vol. 54, p. 8543.

    Article  CAS  Google Scholar 

  22. Lindner, E. and Khanfar, M., J. Organomet. Chem., 2001, vol. 630, p. 244.

    Article  CAS  Google Scholar 

  23. Vysotskaya, O.V., Reutskaya, A.M., and Trofimov, B.A., Abstract of Papers, V Molodezhnnaya shkolakonferenysija po organicheskoi khimii (V Young School-Conf. on Organic Synthesis), Yekaterinburg, 2002, p. 123.

  24. Nawrot, B., Michalak, O., De Clercq, E., and Stec, W.J., Antivir. Chem. Chemother., 2004, vol. 15, no. 6, p. 319.

    CAS  Google Scholar 

  25. Caminade, A.-M., Turrin, C.-O., Laurent, R., Maraval, A., Majoral J.-P., Current Org. Chem., 2006, vol. 10, no. 18, p. 2333.

    Article  CAS  Google Scholar 

  26. Gusarova, N.K., Reutskaya, A.M., Ivanova, N.I., Medvedeva, A.S., Demina, M.M., Novopashin, P.S., Afonin, A.V., Albanov, A.I., and Trofimov, B.A., J. Organomet. Chem., 2002, vol. 659, nos. 1–2, p. 172.

    Article  CAS  Google Scholar 

  27. Ivanova, N.I., Reutskaya, A.M., Gusarova, N.K., Medvedeva, S.A., Afonin, A.V., Ushakov, I.A., Tatarinova, A.A., and Trofimov, B.A., Russ. J. Gen. Chem., 2003, vol. 73, no. 9, p. 1354.

    Article  CAS  Google Scholar 

  28. Ivanova, N.I., Volkov, P.A., Baikalova, L.V., Gusarova, N.K., and Trofimov, B.A., Chem. Heterocycl. Comp., 2008, no. 11, p. 1669.

  29. Ivanova, N.I., Gusarova, N.K., Konovalova, N.A., Volkov, P.A., Levkovskaya, G.G., Larina, L.I., and Trofimov, B.A., Russ. J. Gen. Chem., 2009, vol. 79, no. 10, p. 2102.

    Article  CAS  Google Scholar 

  30. Arbuzova, S.N., Gusarova, N.K., and Trofimov, B.A., Arkivoc, 2006, no. 5, p. 12.

  31. Trofimov, B.A. and Gusarova, N.K., Mendeleev Commun., 2009, no. 19, p. 295.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. I. Ivanova, P. A. Volkov, N. K. Gusarova, L. I. Larina & B. A. Trofimov

Authors
  1. N. I. Ivanova
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  2. P. A. Volkov
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  3. N. K. Gusarova
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  4. L. I. Larina
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  5. B. A. Trofimov
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Corresponding author

Correspondence to N. I. Ivanova.

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Original Russian Text © N.I. Ivanova, P.A. Volkov, N.K. Gusarova, L.I. Larina, B.A. Trofimov, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 2, pp. 215–221.

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Ivanova, N.I., Volkov, P.A., Gusarova, N.K. et al. Directed synthesis of tertiary phosphine chalcogenides with pyridine and hydroxy functions. Russ J Gen Chem 81, 315–321 (2011). https://doi.org/10.1134/S1070363211020071

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  • DOI: https://doi.org/10.1134/S1070363211020071

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