Advertisement

Chemistry of Heterocyclic Compounds

, Volume 51, Issue 10, pp 913–917 | Cite as

Synthesis of 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a,5,6,7,7a-hexahydropyrano[2,3-c]pyrrol-2-ones from 4-aryl-6-(trifluoromethyl)-2-pyrones, sarcosine, and formaldehyde

  • Sergey A. Usachev
  • Natal’ya V. Popova
  • Vladimir S. Moshkin
  • Vyacheslav Ya. SosnovskikhEmail author
Article

4-Aryl-6-(trifluoromethyl)-2-pyrones reacted with the nonstabilized azomethine ylide obtained from sarcosine and formaldehyde under reflux in benzene for 6 h, resulting in [3+2] cycloaddition that gave 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a,5,6,7,7a-hexahydropyrano-[2,3-c]pyrrol-2-ones in 42–56% yields. In the case of 4-aryl-3-carbethoxy-6-(trifluoromethyl)-2-pyrones, besides the respective pyrano-[2,3-c]pyrrolidines (66–71% yields) also 4-aryl-1-methyl-2-(trifluoromethyl)pyrroles were isolated as minor products.

Keywords

azomethine ylides pyrano[2,3-c]pyrrolidines 2-pyrones pyrroles [3+2] cycloaddition 

Notes

This work was performed with financial support from the Russian Scientific Fund (project 14-13-00388).

References

  1. 1.
    (a) Goel, A.; Ram, V. J. Tetrahedron 2009, 65, 7865. (b) Ram, V. J.; Srivastava, P. Curr. Org. Chem. 2001, 5, 571.Google Scholar
  2. 2.
    (a) Dickinson, J. M. Nat. Prod. Rep. 1993, 10, 71. (b) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J. P. Bioorg. Med. Chem. 2004, 12, 4285.Google Scholar
  3. 3.
    Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.CrossRefGoogle Scholar
  4. 4.
    (a) Zheng, S.; Lu, X. Org. Lett. 2009, 11, 3978. (b) Liu, K.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2014, 16, 4508.Google Scholar
  5. 5.
    (a) Trost, B. M.; Schneider, S. Angew. Chem., Int. Ed. 1989, 28, 213. (b) Tokuyama, H.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5523.Google Scholar
  6. 6.
    (a) Groundwater, P. W.; Hibbs, D. E.; Hursthouse, M. B.; Nyerges, M. J. Chem. Soc., Perkin Trans. 1 1997, 163. (b) Rudas, M.; Fejes, I.; Nyerges, M.; Szöllõsy, Á.; Tõke, L.; Groundwater, P. W. J. Chem. Soc., Perkin Trans. 1 1999, 1167.Google Scholar
  7. 7.
    Usachev, B. I.; Obydennov, D. L.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Org. Lett. 2008, 10, 2857.CrossRefGoogle Scholar
  8. 8.
    Yeh, P.-P.; Daniels, D. S. B.; Cordes, D. B.; Slawin, A. M. Z.; Smith, A. D. Org. Lett. 2014, 16, 964.CrossRefGoogle Scholar
  9. 9.
    (a) Usachev, S. A.; Usachev, B. I.; Sosnovskikh, V. Y. Tetrahedron 2014, 70, 60. (b) Usachev, S. A.; Usachev, B. I.; Eltsov, O. S.; Sosnovskikh, V. Y. Tetrahedron 2014, 70, 8863. (c) Usachev, B. I.; Usachev, S. A.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Tetrahedron Lett. 2011, 52, 6723.Google Scholar
  10. 10.
    (a) Moshkin, V. S.; Sosnovskikh, V. Y.; Röschenthaler, G.-V. Tetrahedron 2013, 69, 5884. (b) Korotaev, V. Y.; Barkov, A. Y.; Moshkin, V. S.; Matochkina, E. G.; Kodess, M. I.; Sosnovskikh, V. Y. Tetrahedron 2013, 69, 8602. (c) Sosnovskikh, V. Y.; Kornev, M. Y.; Moshkin, V. S.; Buev, E. M. Tetrahedron 2014, 70, 9253.Google Scholar
  11. 11.
    (a) Bégué, J.-P.; Bonnet-Delpon, D.; Lequeux, T. Tetrahedron Lett. 1993, 34, 3279. (b) Bigotti, S.; Malpezzi, L.; Molteni, M.; Mele, A.; Panzeri, W.; Zanda, M. Tetrahedron Lett. 2009, 50, 2540. (c) Davoren, J. E.; Gray, D. L.; Harris, A. R.; Nason, D. M.; Xu, W. Synlett 2010, 2490. (d) Plancquaert, M.-A.; Redon, M.; Janousek, Z.; Viehe, H. G. Tetrahedron 1996, 52, 4383. (e) Li, Q.; Wang, W.; Berst, K. B.; Claiborne, A.; Hasvold, L.; Raye, K.; Tufano, M.; Nilius, A.; Shen, L. L.; Flamm, R.; Alder, J.; Marsh, K.; Crowell, D.; Chu, D. T. W.; Plattner, J. J. Bioorg. Med. Chem. Lett. 1998, 8, 1953. (f) Fukui, H.; Shibata, T.; Naito, T.; Nakano, J.; Maejima, T.; Senda, H.; Iwatani, W.; Tatsumi, Y.; Suda, M.; Arika, T. Bioorg. Med. Chem. Lett. 1998, 8, 2833. (g) Yarmolchuk, V. S.; Shishkin, O. V.; Starova, V. S.; Zaporozhets, O. A.; Kravchuk, O.; Zozulya, S.; Komarov, I. V.; Mykhailiuk, P. K. Eur. J. Org. Chem. 2013, 3086. (h) Grafton, M.; Mansfield, A. C.; Fray, M. J. Tetrahedron Lett. 2010, 51, 1026.Google Scholar
  12. 12.
    Moshkin, V. S.; Sosnovskikh, V. Y.; Röschenthaler, G.-V. Tetrahedron Lett. 2012, 53, 3568.CrossRefGoogle Scholar
  13. 13.
    Saijo, R.; Hagimoto, Y.; Kawase M. Org. Lett. 2010, 12, 4776.CrossRefGoogle Scholar
  14. 14.
    Lee, J. J.; Pollock, G. R., III; Mitchell, D.; Kasuga, L.; Kraus, G. A. RSC Adv. 2014, 4, 45657.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Sergey A. Usachev
    • 1
  • Natal’ya V. Popova
    • 1
  • Vladimir S. Moshkin
    • 1
  • Vyacheslav Ya. Sosnovskikh
    • 1
    Email author
  1. 1.Institute of Natural SciencesUral Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia

Personalised recommendations