Catalysis Letters

, Volume 148, Issue 6, pp 1651–1658 | Cite as

New Crown Ether-Based Nano Ionic Liquid ([DB-18-C-6K+][OH] nIL): A Versatile Nanocatalyst for the Synthesis of Spiro[indoline-3,2′-quinoline] Derivatives via the Cascade Four-Component Reaction of Arylamines, Dialkylacetylenedicarboxylates, Isatins and Dimedone

  • Kobra Nikoofar
  • Shiva Khani


A new nano-size crown ether-based ionic liquid on the basis of dibenzo-18-crown-6 ([DB-18-C-6K+][OH] nIL) has been synthesized via a simple procedure and characterized through fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, high-resolution scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric/differential thermal analysis, and UV–Vis spectroscopy techniques The obtained catalyst has been utilized for the one-pot, four-component synthesis of spiro[indoline-3,2′-quinoline] derivatives from the combination of isatins, amines, dimedone, and dialkylacetylenedicarboxylates. The advantages of this protocol included the use of common and easily-available starting materials, utilizing ambient temperature, non-toxic and inexpensive reagent usage, high yields of products, and operationally simple procedure.

Graphical Abstract


Crown ether-based nano ionic liquid Spiro[indoline-3,2′-quinoline] Spiro compounds Multi-component reaction Isatin Dialkylacetylenedicarboxylates 



The researchers appreciate Alzahra University research council for partial financial support of this work.

Compliance with Ethical Standards

Conflict of interest

The authors declare that they have no conflict of interest.


  1. 1.
    Parvulescu VI, Hardacre C (2007) Catalysis in ionic liquids. Chem Rev 107(6):2615–2665CrossRefPubMedGoogle Scholar
  2. 2.
    Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC et al (2002) Novel brønsted acidic ionic liquids and their use as dual solvent-catalysts. J Am Chem Soc 124(21):5962–5963CrossRefPubMedGoogle Scholar
  3. 3.
    Amarasekara AS (2016) Acidic ionic liquids. Chem Rev 116(10):6133–6183CrossRefPubMedGoogle Scholar
  4. 4.
    Vafaeezadeh M, Alinezhad H (2016) Brønsted acidic ionic liquids: green catalysts for essential organic reactions. J Mol Liq 218:95–105CrossRefGoogle Scholar
  5. 5.
    Davis JH Jr (2004) Task-specific ionic liquids. Chem Lett 33(9):1072–1077CrossRefGoogle Scholar
  6. 6.
    Yue C, Fang D, Liu L, Yi TF (2011) Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J Mol Liq 163(3):99–121CrossRefGoogle Scholar
  7. 7.
    Singh H, Sindhu J, Khurana JM, Sharma C, Aneja KR (2014) Ultrasound promoted one pot synthesis of novel fluorescent triazolyl spirocyclic oxindoles using DBU based task specific ionic liquids and their antimicrobial activity. Eur J Med Chem 77:145–154CrossRefPubMedGoogle Scholar
  8. 8.
    Galliford CV, Scheidt KA (2007) Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents. Angew Chem 46:8748–8758CrossRefGoogle Scholar
  9. 9.
    Satyamaheshwar P (2009) 3-Substituted-3-hydroxyl-2-oxindole, an emerging new scaffold for drug discovery with potential anticancer and other biological activities. Curr Bioact Compd 5(1):20–38CrossRefGoogle Scholar
  10. 10.
    Yeung BKS, Zou B, Rottmann M, Lakshminarayana SB, Ang SH, Leong SY et al (2010) Spirotetrahydro β-carbolines (spiroindolones): a new class of potent and orally efficacious compounds for the treatment of malaria. J Med Chem 53(14):5155–5164CrossRefPubMedGoogle Scholar
  11. 11.
    Bhaskar G, Arun Y, Balachandran C, Saikumar C, Perumal PT (2012) Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity. Eur J Med Chem 51:79–91CrossRefPubMedGoogle Scholar
  12. 12.
    Liu J, Sun Y, Zhang X, Liang X, Wu Y, Wang Y, Jiang X (2014) Spirooxindoles, a potential novel class of anti-inflammatory agent. Inflamm Cell Signal 1(4):372–375Google Scholar
  13. 13.
    Girgis AS, Mabied AF, Stawinski J, Hegazy L, George RF, Farag H, Shalaby EM (2015) Farag ISA synthesis and DFT studies of an antitumor active spiro-oxindole. New J Chem 39:8017–8027CrossRefGoogle Scholar
  14. 14.
    Sun J, Sun Y, Gao H, Yan C-G (2012) Synthesis of spiro [indoline-3, 2′-quinoline] derivatives through a four-component reaction. Eur J Org Chem 2012(10):1976–1983CrossRefGoogle Scholar
  15. 15.
    Debnath K, Pramanik A (2015) Heterogeneous bimetallic ZnFe2O4 nanopowder catalysed facile four component reaction for the synthesis of spiro[indoline-3,2′-quinoline] derivatives from isatins in water medium. Tetrahedron Lett 56(13):1654–1660CrossRefGoogle Scholar
  16. 16.
    Song Y, Jing H, Li B, Bai D (2011) Crown ether complex cation ionic liquids: preparation and applications in organic reactions. Chem Eur J 17:8731–8738CrossRefPubMedGoogle Scholar
  17. 17.
    Abaszadeh M, Seifi M (2017) Crown ether complex cation ionic liquids: synthesis and catalytic applications for the synthesis of tetrahydro-4H-chromene and 1,4-dihydropyridine derivatives. J Sulfur Chem 38(4):440–449CrossRefGoogle Scholar
  18. 18.
    Shirini F, Langarudi MSN, Seddighi M, Jolodar OG (2015) Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1,8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2,4,6-trione derivatives. Res Chem Intermed 41(11):8483–8497CrossRefGoogle Scholar
  19. 19.
    Xing H, Wang T, Zhou Z, Dai Y (2007) The sulfonic acid-functionalized ionic liquids with pyridinium cations: acidities and their acidity–catalytic activity relationships. J Mol Catal A 264(1–2):53–59CrossRefGoogle Scholar
  20. 20.
    Wang J, Liang Y, Zhou D, Ma J, Jing H (2018) New crown ether complex cation ionic liquids with N-heterocycle anions: preparation and application in CO2 fixation. Org Chem Front 5:741–748CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Chemistry Department, School of Physics and ChemistryAlzahra UniversityTehranIran

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