Advertisement

Tandem Approach to Functionalized Pyrrolo[3,4-a]carbazole-1,3-diones via a Pd-catalyzed Indole-to-carbazole Transformation

  • Lianghua Guo
  • Mei Xu
  • Yong Jian
  • Sheng Liu
  • Weidong PanEmail author
  • Lian DuanEmail author
Article
  • 5 Downloads

Abstract

A one-pot and efficient three-component reaction of indoles, acrylates and maleimides for the synthesis of pyrrolo[3,4-a]carbazole-1,3-dione derivatives was developed. Theree C-C bonds and one ring were created in a single step via an indole-to-carbazole transformation triggered by Pd(II)-catalyzed direct C3-alkenylation of indoles.

Keywords

Carbazole One-pot Tandem reaction Three-component reaction Indole-to-carbazole 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

40242_2019_8399_MOESM1_ESM.pdf (949 kb)
A Tandem Approach to Functionalized Pyrrolo[3,4-a]carbazole-1,3-diones via an Pd-catalyzed Indole-to-carbazole Transformation

References

  1. [1]
    Schmidt A. W., Reddy K. R., Knölker H. J., Chem. Rev., 2012, 112, 3193CrossRefGoogle Scholar
  2. [2]
    Tsutsumi L. S., Gündisch D., Sun D. Q., Curr. Top. in Med. Chem., 2016, 16, 1290CrossRefGoogle Scholar
  3. [3]
    Gluszynska A., Eur. J. Med. Chem., 2015, 94, 405CrossRefGoogle Scholar
  4. [4]
    Joseph B., Facompré M., Costa H. D., Routier S., Mérour J. Y., Colson P., Houssier C., Bailly C., Bioorg. Med. Chem., 2001, 9, 1533CrossRefGoogle Scholar
  5. [5]
    Conchon E., Anizon F., Golsteyn R. M., Léonce S., Pfeiffer B., Prudhomme M., Tetrahedron, 2006, 62, 11136CrossRefGoogle Scholar
  6. [6]
    Conchon E., Anizon F., Aboab B., Golsteyn R. M., Léonce S., Pfeiffer B., Prudhomme M., Eur. J. Med. Chem., 2008, 43, 282CrossRefGoogle Scholar
  7. [7]
    Ty N., Dupeyre G., Chabot G. G., Seguin J., Quentin L., Chiaroni A., Tillequin F., Scherman D., Michel S., Cachet X., Eur. J. Med. Chem., 2010, 45, 3726CrossRefGoogle Scholar
  8. [8]
    Pfeuffer L., Pindur U., Helvetica Chimica Acta, 1987, 70, 1419CrossRefGoogle Scholar
  9. [9]
    Pindur U., Kim N. H., Eitel M., Tetrahedron Lett., 1990, 31, 1551CrossRefGoogle Scholar
  10. [10]
    Pindur U., Christian O., Tetrahedron, 1992, 48, 3515CrossRefGoogle Scholar
  11. [11]
    Noland W. E., Walhstrom M. J., Konkel M. J., Brigham M. E., Trowbridge A. G., Konkel L. M. C., Gourneau R. P., Scholten C. A., Lee N. H., Condoluci J. J., Gac T. S., Pour M. M., Radford P. M., J. Heterocyclic. Chem., 1992, 30, 81CrossRefGoogle Scholar
  12. [12]
    Biswas S., Dagar A., Srivastava A., Samanta S., Eur. J. Org. Chem., 2015, 4493Google Scholar
  13. [13]
    Neo A. G., Bornadiego A., Diaz J., Marcaccini S., Marcos C. F., Org. Biomol. Chem., 2013, 11, 6546CrossRefGoogle Scholar
  14. [14]
    Grimster N. P., Gauntlett C., Godfrey C. R. A., Gaunt M. J., Angew. Chem. Int. Ed., 2005, 44, 3125CrossRefGoogle Scholar
  15. [15]
    Chen W. L., Gao Y. R., Mao S., Zhang Y. L., Wang Y. F., Wang Y. Q., Org. Lett., 2012, 14, 5920CrossRefGoogle Scholar
  16. [16]
    Ozaki K., Zhang H., Ito H., Lei A., Itami K., Chem. Sci., 2013, 4, 3416CrossRefGoogle Scholar
  17. [17]
    Verma A. K., Danodia A. K., Saunthwa R. K., Patel M., Choudhary D., Org. Lett., 2015, 17, 3658CrossRefGoogle Scholar
  18. [18]
    Laha J. K., Dayal N., Org. Lett., 2015, 17, 4742CrossRefGoogle Scholar
  19. [19]
    Lin K., Jian Y., Zhao P., Zhao C. S., Pan W. D., Liu S., Org. Chem. Front., 2018, 5, 590CrossRefGoogle Scholar
  20. [20]
    An Y. L., Yang Z. H., Zhang H. H., Zhao S. Y., Org. Lett., 2016, 18, 152CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Functions and Applications of Medicinal PlantsGuizhou Medical UniversityGuiyangP. R. China

Personalised recommendations