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 ZhangEmail author
  • Ziqi Zheng
  • Tong Zhang
  • Xue Fu
  • Shaojia Shi
  • Lin Jiang
  • Hongzong YinEmail author


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.


Dimerazation Pyrroloindole Benzoheterole Pyrrole 


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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

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