Advertisement

Russian Journal of Organic Chemistry

, Volume 55, Issue 5, pp 650–654 | Cite as

Three-Component Spiro Heterocyclization of Pyrrolediones, Indane-1,3-dione, and Heterocyclic Enamines

  • T. V. Salnikova
  • M. V. Dmitriev
  • A. N. MaslivetsEmail author
Article
  • 13 Downloads

Abstract

3-Methyl-2′,5-dioxo-5′-phenyl-1′,2′,5,10-tetrahydrospiro(indeno[1,2-b]isoxazolo[4,3-e]pyridine-4,3′-pyrroles) and 2′,5-dioxo-5′-phenyl-1′,2′,5,10-tetrahydro-1H-spiro(indeno[1,2-b]pyrazole[4,3-e]pyridine-4,3′-pyrroles) are formed via three-component spiro heterocyclization of 4-(ethoxycarbonyl)-5-phenyl-1Hpyrrole-2,3-diones and indane-1,3-dione with 5-amino-3-methylisoxazole or 5-amino-1H-pyrazoles.

Keywords

1H-pyrrole-2,3-diones three-component reactions spiro heterocyclization dihydropyridines enamines 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Cooper, K., Fray, M.J., Cross, P.E., and Richardson, K. EU Patent no. 299727, 1989.Google Scholar
  2. 2.
    Miri, R., Javidnia, K., Hemmateenejad, B., Azarpira, A., and Amirghofran, Z., Bioorg. Med. Chem., 2004, vol. 12, p. 2529. doi  https://doi.org/10.1016/j.bmc.2004.03.032 CrossRefPubMedGoogle Scholar
  3. 3.
    Wang, X.-S., Zhang, M.-M., Jiang, H., Yao, C.-S., and Tu, S.-J., Tetrahedron, 2007, vol. 63, p. 4439. doi  https://doi.org/10.1016/j.tet.2007.03.068 CrossRefGoogle Scholar
  4. 4.
    Samai, S., Nandi, G.C., Kumar, R., and Singh, M.S., Tetrahedron Lett., 2009, vol. 50, p. 7096. doi  https://doi.org/10.1016/j.tetlet.2009.10.022 CrossRefGoogle Scholar
  5. 5.
    Debnath, K., Singha, K., and Pramanik, A., RSC Adv., 2015, vol. 5, p. 31866. doi  https://doi.org/10.1039/C5RA00737B.CrossRefGoogle Scholar
  6. 6.
    Rad-Moghadam, K. and Youseftabar-Miri, L., J. Fluorine Chem., 2012, vol. 135, p. 213. doi  https://doi.org/10.1016/j.jfluchem.2011.11.007 CrossRefGoogle Scholar
  7. 7.
    Dmitriev, M.V., Salnikova, T.V., Silaichev, P.S., and Maslivets, A.N., Tetrahedron Lett., 2017, vol. 58, p. 67. doi  https://doi.org/10.1016/j.tetlet.2016.11.100 CrossRefGoogle Scholar
  8. 8.
    Sano, T., Horiguchi, Y., Toda, J., Imafuku, K., and Tsuda, Y., Chem. Pharm. Bull., 1984, vol. 32, p. 497. doi  https://doi.org/10.1248/cpb.32.497 CrossRefGoogle Scholar
  9. 9.
    CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET).Google Scholar
  10. 10.
    Sheldrick, G.M., Acta Cryst., 2008, vol. A64, p. 112. doi  https://doi.org/10.1107/S0108767307043930 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • T. V. Salnikova
    • 1
  • M. V. Dmitriev
    • 1
  • A. N. Maslivets
    • 1
    Email author
  1. 1.Perm State UniversityPermRussia

Personalised recommendations