Skip to main content
Log in

Green route for the synthesis of 3-substituted indoles using [bmim]HSO4 as non-halogenated ionic liquid

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

In this paper, an effective procedure is reported for the synthesis of 3-substituted indoles via the one-pot three-component reaction of an aldehyde, malononitrile or ethyl cyanoacetate and indole in the presence of [bmim]HSO4 in ethanol under reflux condition. The advantages of this protocol are the synthesis of some novel 3-substituted indoles containing furyl, 4-hydroxyphenyl, and styryl nuclei that are very important in pharmaceutical and drug discovery research in comparison to previously reported results, and the use of non-halogenated ionic liquid.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Nunes PSG, Vidal HAD, Corrêa AG (2020) Org Biomol Chem 18:7751. https://doi.org/10.1039/d0ob01631d

    Article  CAS  PubMed  Google Scholar 

  2. Lamberth C (2020) Bioorg Med Chem 28:115471. https://doi.org/10.1016/j.bmc.2020.115471

    Article  CAS  PubMed  Google Scholar 

  3. (a) Domling A (2006) Chem Rev 106:17. https://doi.org/10.1021/cr0505728; (b) Toure BB, Hall DG (2009) Chem Rev 109:4439. https://doi.org/10.1021/cr800296p

  4. Schreiber SL (2000) Science 287:1964. https://doi.org/10.1126/science.287.5460.1964

    Article  CAS  PubMed  Google Scholar 

  5. Carballares S, Espinosa JF (2005) Org Lett 7:2329. https://doi.org/10.1021/ol050553k

    Article  CAS  PubMed  Google Scholar 

  6. Domling A, Wang W, Wang K (2012) Chem Rev 112:3083. https://doi.org/10.1021/cr100233r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Shiri M (2012) Chem Rev 112:3508. https://doi.org/10.1021/cr2003954

    Article  CAS  PubMed  Google Scholar 

  8. Rajesh UC, Wang J, Prescott S, Tsuzuki T, Rawat DS (2015) ACS Sustain Chem Eng 3:9. https://doi.org/10.1021/sc500594w

    Article  CAS  Google Scholar 

  9. Kumar A, Gupta MK, Kumar M (2012) Green Chem 14:290. https://doi.org/10.1039/c1gc16297g

    Article  CAS  Google Scholar 

  10. Qu Y, Ke F, Zhou L, Li Z, Xiang H, Wu D, Zhou X (2011) Chem Commun 47:3912. https://doi.org/10.1039/c0cc05695b

    Article  CAS  Google Scholar 

  11. Wang L, Huang M, Zhu X, Wan Y (2013) Appl Catal A Gen 454:160. https://doi.org/10.1016/j.apcata.2012.12.008

    Article  CAS  Google Scholar 

  12. He Y-H, Cao J-F, Li R, Xiang Y, Yang D-C, Guan Z (2015) Tetrahedron 71:9299. https://doi.org/10.1016/j.tet.2015.10.027

    Article  CAS  Google Scholar 

  13. Anselmo D, Escudero-Ad EC, Martínez Belmonte M, Kleij AW (2012) Eur J Inorg Chem 2012:4694. https://doi.org/10.1002/ejic.201200150

    Article  CAS  Google Scholar 

  14. Vekariya RL (2017) J Mol Liq 227:44. https://doi.org/10.1016/j.molliq.2016.11.123

    Article  CAS  Google Scholar 

  15. Shekarchi M, Behbahani FK (2020) Russ J Org Chem 56:894. https://doi.org/10.1134/s1070428020050243

    Article  CAS  Google Scholar 

  16. Mohammadi B, Behbahani FK, Marandi GB, Mirza B (2021) Phosphorus. Sulfur Silicon Relat Elem 196:54. https://doi.org/10.1080/10426507.2020.1800702

    Article  CAS  Google Scholar 

  17. Bahekar SS, Kotharkar SA, Shinde DB (2004) Mendeleev Commun 14:210. https://doi.org/10.1070/mc2004v014n05abeh001895

    Article  Google Scholar 

  18. Totten GE, Shah R, Forester D (2019) Fuels and lubricants handbook: technology, properties, performance, and testing, 2nd edn. Portland State University Library. https://doi.org/10.1520/mnl37-2nd-eb

    Book  Google Scholar 

  19. Ghohe N, Tayebee M, Amini R, Mostafa M, Osatiashtiani A, Isaacs MA, Lee AF (2017) Tetrahedron 73:5862. https://doi.org/10.1016/j.tet.2017.08.030

    Article  CAS  Google Scholar 

  20. Omidi M, Amrollahi MA (2017) C R Chimie 20:549. https://doi.org/10.1016/j.crci.2016.09.004

    Article  CAS  Google Scholar 

  21. Pradhan S, Saha JM (2017) New J Chem 41:6616. https://doi.org/10.1039/c7nj00249a

    Article  CAS  Google Scholar 

  22. Jiang H, Wang L, Xie J (2016) J Chem Res 40:338. https://doi.org/10.3184/174751916x14622783380474

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Farahnaz K. Behbahani.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 3399 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shekarchi, M., Behbahani, F.K. & Shekarchi, M. Green route for the synthesis of 3-substituted indoles using [bmim]HSO4 as non-halogenated ionic liquid. Monatsh Chem 152, 659–664 (2021). https://doi.org/10.1007/s00706-021-02782-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02782-y

Keywords

Navigation