Russian Journal of Organic Chemistry

, Volume 46, Issue 11, pp 1709–1718 | Cite as

Synthesis of 7-(furan-2-yl)-7,8,10,10a-tetrahydro-6H-benzo[c]-chromen-6,9(6aH)-diones

  • E. E. Shults
  • S. P. Bondarenko
  • M. M. Shakirov
  • I. Yu. Bagryanskaya
  • G. A. Tolstikov


Methods of synthesis were developed for 7-(furan-2-yl)-substituted 7,8,10,10a-tetrahydrobenzo[c] chromen-6,9-diones by regioselective [4+2]-cycloaddition of coumarin-3-carboxylic acids to 2-(3-trimethylsiloxybuta- 1,3-dien-1-yl)furans. The [4+2]-cycloaddition was efficiently catalyzed with L-proline.


Diene Dione Furan Compound XIII Compound XVII 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Newman, D.J., Cragg, G.M., and Snader, K.M., Nat. Prod. Rep., 2000, vol. 17, p. 215.CrossRefGoogle Scholar
  2. 2.
    Pertwee, R.G., Prog. Neurobiol., 2001, vol. 63, p. 569; Eubanks, L.M., Rogers, C.J., Beuscher, IV, A.E., Koob, G.F., Olson, A.J., Dicker-son, T.J., and Janda, K.D., Molecular Pharmaceutics., 2006, vol. 3, p. 773.CrossRefGoogle Scholar
  3. 3.
    Russo, E.B., Guy, G.W., and Robson, P.J., Chem. Biodiversity, 2007, vol. 4, p. 1729; Butler, M.S., Nat. Prod. Rep., 2008, vol. 25, p. 475.CrossRefGoogle Scholar
  4. 4.
    Wilson, R.S., May, E.L., Martin, B.R., and Dewey, W.K., J. Med. Chem., 1976, vol. 19, p. 1165; Melvin, L.S., Bordner, J., Hada, J.B., and Johnson, M.R., J. Heterocycl. Chem., 1990, vol. 27, p. 535; Trost, B.M. and Dogra, K., Org. Lett., 2007, vol. 9, p. 861; Song, Y., Hwang, S., Gong, P., Kim, D., and Kim, S., Org. Lett., 2008, vol. 10, p. 269.CrossRefGoogle Scholar
  5. 5.
    Bonsignore, L., Cottiglia, F., Maccioni, A.M., Seca, D., and Lavagna, S.M., J. Heterocycl. Chem., 1986, vol. 32, p. 573.CrossRefGoogle Scholar
  6. 6.
    Bigi, F., Chesini, L., Maggi, R., and Sartori, G., J. Org. Chem., 1999, vol. 64, p. 1033.CrossRefGoogle Scholar
  7. 7.
    Armstrong, V., Soto, O., Valderrama, A., and Tapia, R., Synth. Commun., 1988, vol. 18, p. 717.CrossRefGoogle Scholar
  8. 8.
    Bandgar, B.P., Uppalla, L.S., and Kurule, D.S., Green Chem., 1999, p. 243; Scott, J.L. and Raston, C.L., Green Chem., 2000, vol. 2, p. 245.Google Scholar
  9. 9.
    Song, A., Wang, X., and Lam, K.S., Tetrahedron Lett., 2003, vol. 44, p. 1755.CrossRefGoogle Scholar
  10. 10.
    Maggi, R., Bigi, F., Carloni, S., Mazzacani, A., and Sartori, G., Creen Chem., 2001, vol. 3, p. 173; Deshmukh, M.N., Burud, R., Baldino, K., Chan, P.C.M., and Liu, J., Synth. Commun., 2003, vol. 33, p. 3299.Google Scholar
  11. 11.
    Darvatkar, N.B., Deorukhkar, A.R., Bhilare, S.V., Raut, D.G., and Salunkhe, M.M., Synth. Commun., 2008, vol. 38, p. 3508.CrossRefGoogle Scholar
  12. 12.
    Taylor, E.C. and Strojny, E.J., J. Am. Chem. Soc., 1960, vol. 82, p. 5198.CrossRefGoogle Scholar
  13. 13.
    Ohkata, K., Miyamoto, K., Matsumura, S., and Akiba, K., Tetrahedron Lett., 1993, vol. 34, p. 6575.CrossRefGoogle Scholar
  14. 14.
    Fringuelli, F., Girotti, R., Pizzo, F., Zunino, E., and Vaccaro, L., Adv. Synth. Catal., 2006, vol. 348, p. 297.CrossRefGoogle Scholar
  15. 15.
    Girotti, R., Marrocchi, A., Minuti, L., Piermatti, O., Pizzo, F., and Vaccaro, L., J. Org. Chem., 2006, vol. 71, p. 70.CrossRefGoogle Scholar
  16. 16.
    Minuti, L., Marrocchi, A., Landi, S., Seri, M., and Gacs-Baitz, E., Tetrahedron, 2007, vol. 63, p. 5477; Ballerini, E., Minuti, L., Piermatti, O., and Pizzo, F., J. Org. Chem., 2009, vol. 74, p. 4311.CrossRefGoogle Scholar
  17. 17.
    Shults, E.E., Semenova, E.A., Johnson, A.A., Bondarenko, S.P., Bagryanskaya, I.Y., Gatilov, Y.V., Tolstikov, G.A., and Pommier, Y., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 1362.CrossRefGoogle Scholar
  18. 18.
    Allen, F.H., Kenard, O., Watson, D.G., Bramer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. 1.Google Scholar
  19. 19.
    Allen, F.H. and Kenard, O., Chem. Des. Automat. News, 1993, vol. 8, p. 31.Google Scholar
  20. 20.
    Collins, D.J., Fallon, G.D., Staffa, A., and Tope, H., Aust. J. Chem., 1996, vol. 49, p. 719.CrossRefGoogle Scholar
  21. 21.
    Davidson, D. and Bernhard, S.A., J. Am. Chem. Soc., 1948, vol. 70, p. 3426.CrossRefGoogle Scholar
  22. 22.
    Tolstikov, G.A., Shul’ts, E.E., Safarova, G.M., Spirikhin, L.V., and Panasenko, A.A., Zh. Org. Khim., 1990, vol. 26, p. 1283.Google Scholar
  23. 23.
    Sheldrick, G.M., SHELX-97, release, 97-2, University of Göttingen, Germany, 1998.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • E. E. Shults
    • 1
  • S. P. Bondarenko
    • 1
  • M. M. Shakirov
    • 1
  • I. Yu. Bagryanskaya
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia

Personalised recommendations