Advertisement

Chemical Research in Chinese Universities

, Volume 34, Issue 4, pp 559–563 | Cite as

Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles

  • Shuai Zhang
  • Ziqi Zheng
  • Tong Zhang
  • Xue Fu
  • Shaojia Shi
  • Lin Jiang
  • Hongzong Yin
Article
  • 7 Downloads

Abstract

Pyrroloindoles, as a kind of promising small-melecular hole injetion materials, have attracted wide attention. Herein, we described a simple metal-free method for the synthesis of 4,8-dihydropyrrolo[2,3-f]indole compounds through the acid-catalyzed dimerization reaction of pyrroles. The structures of target 4,8-dihydropyrrolo-[2,3-f]indoles were confirmed by NMR spectrum and X-ray single crystal diffraction. Notably, pyrrole substrates were synthesized conveniently starting from available biological dipeptides. cis-Configuration was preferred when bulky p-toluene sulfonic acid(TsOH) was employed. Excessive aicds empoyed in dimerization would lead to the formation of quantitative pyrrolium chloride intermediate, restraining further conversion to target compounds. Furthermore, the dimerization process was monitored by 1H NMR spectrum, proving that it followed a second-order kinetics, providing significant insight to the mechanism of dimerization reaction.

Keywords

Dimerazation Pyrroloindole Benzoheterole Pyrrole 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    Anderson S., Taylor P. N., Verschoor G. L. B., Chem. Eur. J., 2004, 10, 518CrossRefGoogle Scholar
  2. [2]
    Nozaki K., Takahashi K., Nakano K., Hiyama T., Tang H. Z., Fujiki M., Yamaguchi S., Tamao K., Angew. Chem. Int. Ed., 2003, 42, 2051CrossRefGoogle Scholar
  3. [3]
    Xu C., Wakamiya A., Yamaguchi S., Org. Lett., 2004, 6, 3707CrossRefGoogle Scholar
  4. [4]
    de Bettignies R., Nicolas Y., Blanchard P., Levillain E., Nunzi J. M., Roncali J., Adv. Mater., 2003, 15, 1939CrossRefGoogle Scholar
  5. [5]
    Wang C., Sperry J., Synlett., 2012, 23, 1824CrossRefGoogle Scholar
  6. [6]
    Chunchatprasert L., Shannon P. V., J. Chem. Soc., Perkin Trans. I, 1996, 1787Google Scholar
  7. [7]
    Chen H. Z., Jin Y. D., Xu R. S., Peng B. X., Desseyn H., Janssens J., Heremans P., Borghs G., Geise H. J., Synthetic Metals, 2003, 139, 529CrossRefGoogle Scholar
  8. [8]
    Tsuji H., Mitsui C., Ilies L., Sato Y., Nakamura E., J. Am. Chem. Soc., 2007, 129, 11902CrossRefGoogle Scholar
  9. [9]
    Tsuji H., Yokoi Y., Furukawa S., Nakamura E., Heterocycles, 2015, 90, 261CrossRefGoogle Scholar
  10. [10]
    Nakamura T., Furukawa S., Nakamura E., Chem. Asian J., 2016, 11, 2016CrossRefGoogle Scholar
  11. [11]
    Salzner U., Lagowski J. B., Pickup P. G., Poirier R. A., Synth. Met., 1998, 96, 177CrossRefGoogle Scholar
  12. [12]
    Katritzky A. R., Li J., Stevens C. V., J. Org. Chem., 1995, 60, 3401CrossRefGoogle Scholar
  13. [13]
    Gu R., Snick S. V., Robeyns K., Meervelt L. V., Dehaen W., Org. Biomol. Chem., 2009, 7, 380CrossRefGoogle Scholar
  14. [14]
    Crigoras M., Negru O. I., Rev. Chim. Bucharest, 2016, 67(3), 430Google Scholar
  15. [15]
    Park I. K., Suh S. E., Lim B. Y., Cho C. G., Org. Lett., 2009, 11, 5454CrossRefGoogle Scholar
  16. [16]
    Tsuji H., Yokoi Y., Mitsui C., Ilies L., Sato Y., Nakamura E., Chem. Asian J., 2009, 4, 655CrossRefGoogle Scholar
  17. [17]
    Visconti A., Moody C. J., Heterocycles, 2014, 88, 705CrossRefGoogle Scholar
  18. [18]
    Clentsmith G. K. B., Field L. D., Messerle B. A., Shasha A., Turner P., Tetrahedron Lett., 2009, 50, 1469CrossRefGoogle Scholar
  19. [19]
    Bodanszky M., Bodanszky A., The Practice of Peptide Synthesis, 2nd Edition, Springer-Verlag, New York, 1995, 118Google Scholar
  20. [20]
    Rebek Jr. J., fsGehret J. C. E., Tetrahedron Lett., 1977, 18, 3027CrossRefGoogle Scholar
  21. [21]
    Wallington T. J., Schneider W. F., Barnes I., Becker K. H., Sehested J., Nielsen O. J., Chem. Phys. Lett., 2000, 322, 97CrossRefGoogle Scholar
  22. [22]
    Peña L. A., Hoggard P. E., J. Mol. Catal. A: Chem., 2010, 327, 20CrossRefGoogle Scholar
  23. [23]
    Wu X. Z., Yamamoto T., Hatashita M., Bull. Chem. Soc. Jpn., 2002, 75, 2527CrossRefGoogle Scholar

Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.College of Chemistry and Material ScienceShandong Agricultural UniversityTaianP. R. China

Personalised recommendations