Russian Journal of Organic Chemistry

, Volume 41, Issue 12, pp 1824–1835 | Cite as

Synthesis of New Derivatives of Protoporphyrin IX and Chlorophyll a

  • V. Yu. Pavlov
  • I. O. Konstantinov
  • G. V. Ponomarev
  • V. P. Timofeev
  • B. G. Kimel'


The vinyl groups in protoporphyrin IX and chlorophyll a derivatives were selectively transformed into hydroxymethyl and acetoxymethyl substituents. The reactivities of β-hydroxymethyl and β-acetoxymethyl groups in porphyrins and chlorins toward nucleophilic reagents were compared for the first time using the reaction with acetylacetone as an example. Peripheral acetylacetone moieties in porphyrins and chlorins were shown to be promising as building blocks for generation of exo heterocyclic structures.


Chlorophyll Organic Chemistry Chlorin Vinyl Porphyrin 
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  1. 1.
    Ponomarev, G.V., Pavlov, V.Yu., Konstantinov, I.O., Timofeev, V.P., and Kimel', B.G., Russ. J. Org. Chem., 2003, vol. 39, p. 1683.CrossRefGoogle Scholar
  2. 2.
    Smith, K.M. and Cavaleiro, J.A.S., Heterocycles, 1987, vol. 26, p. 1947.Google Scholar
  3. 3.
    Sternberg, E.D., Dolphin, D., and Bruckner, C., Tetrahedron, 1998, vol. 54, p. 4151.CrossRefGoogle Scholar
  4. 4.
    Ali, H. and van Lier, J.E., Chem. Rev., 1999, vol. 99, p. 2379.CrossRefGoogle Scholar
  5. 5.
    Mody, T.D., J. Porphyrins Phthalocyanines, 2000, vol. 4, p. 362.CrossRefGoogle Scholar
  6. 6.
    Pandey, R.K., J. Porphyrins Phthalocyanines, 2000, vol. 4, p. 368.CrossRefGoogle Scholar
  7. 7.
    Vicente, M.G.H. and Smith, K.M., Curr. Org. Chem., 2000, vol. 4, p. 139.CrossRefGoogle Scholar
  8. 8.
    Arnold, D.P., Johnson, A.W., and Winter, M., J. Chem. Soc., Chem. Commun., 1976, p. 797.Google Scholar
  9. 9.
    Ponomarev, G.V., Khim. Geterotsikl. Soedin., 1977, vol. 13, p. 90.Google Scholar
  10. 10.
    Bushell, M.J., Evans, B., Kenner, G.W., and Smith, K.M., Heterocycles, 1977, vol. 7, p. 67.Google Scholar
  11. 11.
    Smith, K.M., Bisset, G.M.F., and Bushell, M.J., Bioorg. Chem., 1980, vol. 9, p. 1.CrossRefGoogle Scholar
  12. 12.
    Gilchrist, T.L., Heterocyclic Chemistry, Harlow, Essex: Longman Scientific & Technical, 1992, 2nd ed.Google Scholar
  13. 13.
    Porphyrins and Metalloporphyrins, Smith, K.M., Ed., Amsterdam: Elsevier, 1975.Google Scholar
  14. 14.
    Pavlov, V.Yu., Kabachnik, M.M., Zobnina, E.V., Timofeev, V.P., Konstantinov, I.O., Kimel, B.G., Ponomarev, G.V., and Beletskaya, I.P., Synlett, 2003, p. 2193.Google Scholar
  15. 15.
    Smith, K.M. and Bisset, G.M.F., J. Org. Chem., 1979, vol. 44, p. 2077.Google Scholar
  16. 16.
    Smith, K.M., Goff, D.A., and Simpson, D.J., J. Am. Chem. Soc., 1985, vol. 107, p. 4946.Google Scholar
  17. 17.
    Pandey, R.K., Isaac, M., MacDonald, I., Medforth, C.J., Senge, M.O., Dougherty, T.J., and Smith, K.M., J. Org. Chem., 1997, vol. 62, p. 1463.Google Scholar
  18. 18.
    Ponomarev, G.V., Khim. Geterotsikl. Soedin., 1994, vol. 30, p. 1669.Google Scholar
  19. 19.
    Arnold, D.P., Johnson, A.W., and Winter, M., J. Chem. Soc., Perkin Trans. 1, 1977, p. 1643.Google Scholar
  20. 20.
    Smith, K.M. and Bisset, G.M.F., J. Chem. Soc., Perkin Trans. 1, 1981, p. 2625.Google Scholar
  21. 21.
    Ponomarev, G.V., Kirillova, G.V., and Yashunskii, D.V., Khim. Geterotsikl. Soedin., 2000, no. 9, p. 1197.Google Scholar
  22. 22.
    Valles, M.A., Afinidad, 1993, vol. 448, p. 469.Google Scholar
  23. 23.
    Kozyrev, A.N., Zheng, G., Shibata, M., Alderfer, J.L., Dougherty, T.J., and Pandey, R.K., Org. Lett., 1999, p. 1193.Google Scholar
  24. 24.
    Cox, GS. and Whiten, D.G., J. Am. Chem. Soc., 1982, vol. 104, p. 516.Google Scholar
  25. 25.
    Brault, D., Vever-Bizet, C., Rougee, M., and Bensasson, R., J. Photochem. Photobiol., 1988, vol. 47, p. 151.Google Scholar
  26. 26.
    Aveline, B., Delgado, O., and Brault, D., J. Chem. Soc., Faraday Trans., 1992, vol. 88, p. 1971.CrossRefGoogle Scholar
  27. 27.
    Grandadam, M., Ingrand, D., Huraux, J.-M., Aveline, B., Delgado, O., Vever-Bizet, C., and Brault, D., J. Photochem. Photobiol. B, 1995, vol. 31, p. 171.CrossRefGoogle Scholar
  28. 28.
    Boutorine, A.S., Brault, D., Takasugi, M., Delgado, O., and Helene, C., J. Am. Chem. Soc., 1996, vol. 118, p. 9469.CrossRefGoogle Scholar
  29. 29.
    Iakovides, P. and Smith, K.M., Tetrahedron, 1996, vol. 52, p. 1123.CrossRefGoogle Scholar

Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • V. Yu. Pavlov
    • 1
    • 2
  • I. O. Konstantinov
    • 3
  • G. V. Ponomarev
    • 3
  • V. P. Timofeev
    • 4
  • B. G. Kimel'
    • 5
  1. 1.Faculty of ChemistryMoscow State UniversityMoscowRussia
  2. 2.Lomonosov Moscow State Academy of Chemical TechnologyMoscowRussia
  3. 3.“Orekhovich Research Institute” State EnterpriseRussian Academy of Medical SciencesMoscowRussia
  4. 4.Engel'gardt Institute of Molecular BiologyRussian Academy of SciencesMoscowRussia
  5. 5.Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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