Skip to main content
Log in

HNO3@nano SiO2 Catalyzed Green and Efficient Synthesis of Symmetrical and Unsymmetrical Di(indolyl)indoline-2-ones by Stirring and Grindstone Methods

  • Short Communication
  • Published:
National Academy Science Letters Aims and scope Submit manuscript

Abstract

A simple, efficient, solvent-free, and mild method for the preparation of di(indolyl)indoline-2-ones (symmetrical and unsymmetrical), have been reported in the presence of HNO3@nano SiO2 under both stirring and grinding techniques at room temperature successfully.

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.

Scheme 1
Fig. 1

References

  1. Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y (2006) Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2. Bioorg Med Chem Lett 109:2109–2112

    Article  Google Scholar 

  2. Chen LR, Wang YCh, Lin YW, Chou Sh, Chen Sh, Liu LT, Wu YT, Kuo Ch, Chen Juang Sh (2005) Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. Bioorg Med Chem Lett 15:3058–3062

    Article  CAS  Google Scholar 

  3. Denoyelle S, Chen T, Yang H, Chen L, Zhang Y, Halperin JA, Aktas BH, Chorev M (2013) Synthesis and SAR study of novel 3,3-diphenyl-1,3-dihydroindol-2-one derivatives as potent eIF2·GTP·Met-tRNAiMet ternary complex inhibitors. Eur J Med Chem 69:537–553

    Article  CAS  Google Scholar 

  4. Tripathy R, Reiboldt A, Messina PA, Iqbal M, Singh J, Bacon ER, Angeles Th, Yang Sh, Albom MS, Robinson C, Chang H, Ruggeri BA, Mallamo JP (2006) Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis. Bioorg Med Chem Lett 16:2158–2161

    Article  CAS  Google Scholar 

  5. Azizian J, Mohammadi AA, Karimi N, Mohammadizadeh MR, Karimi AR (2006) Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives. Catal Commun 7:752–755

    Article  CAS  Google Scholar 

  6. Kumar A, Shukla RD, Yadav D, Gupta LP (2015) Friedel–Crafts alkylation of indoles in deep eutectic solvent. RSC Adv 5:52062–52065

    Article  CAS  Google Scholar 

  7. Saffar-Teluri A (2014) Boron trifluoride supported on nano-SiO2: an efficient and reusable heterogeneous catalyst for the synthesis of bis(indolyl)methanes and oxindole derivatives. Res Chem Intermed 40:1061–1067

    Article  CAS  Google Scholar 

  8. Subba Reddy BV, Rajeswari N, Sarangapani M, Prashanthi Y, Ganji RJ, Addlagatta A (2012) Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl) indolin-2-ones and evaluation of their cytotoxicity. Bioorg Med Chem Lett 22:2460–2463

    Article  CAS  Google Scholar 

  9. Alimohammadi K, Sarrafi Y, Tajbakhsh M (2008) H6P2W18O62: a green and reusable catalyst for the synthesis of 3,3-diaryloxindole derivatives in water. Monatsh Chem 139:1037–1039

    Article  CAS  Google Scholar 

  10. Wang Sh, Ji Sh (2006) Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation. Tetrahedron 62:1527–1530

    Article  CAS  Google Scholar 

  11. Nikpasand M, Mamaghani M, Tabatabaeian Kh, Samimi HA (2010) An efficient and clean synthesis of symmetrical and unsymmetrical 3,3-di(indolyl) indolin-2-ones using KSF. Synth Commun 40:3552–3560

    Article  Google Scholar 

  12. Rad-Moghadam K, Sharifi-Kiasaraie M, Taheri-Amlashi H (2010) Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl) indolin-2-ones under controlled catalysis of ionic liquids. Tetrahedron 66:2316–2319

    Article  CAS  Google Scholar 

  13. Khodaei MM, Mohammadpoor-Baltork I, Memarian HR, Khosropour AR, Nikoofar K, Ghanbary P (2008) Synthesis of 3-substituted indoles promoted by pulverization-activation method catalyzed by Bi(NO3)3·5H2O. J Heterocycl Chem 45:377–381

    Article  CAS  Google Scholar 

  14. Ghanbari K, Nikoofar K (2014) Electrosynthesis of 3,3-di (indolyl) indolin-2-one nanorods. Monatsh Chem 145:1867–1871

    Article  CAS  Google Scholar 

  15. Haghighi M, Nikoofar K (2016) Nano TiO2/SiO2: an efficient and reusable catalyst for the synthesis of oxindole derivatives. J Saudi Chem Soc 20:101–106

    Article  CAS  Google Scholar 

  16. Nikoofar K, Khalili Z (2016) Nano-SiO2: a heterogeneous and reusable catalyst for the one-pot synthesis of symmetrical and unsymmetrical 3,3-di(aryl)indolin-2-ones under solvent-free conditions. Z Naturforsch 1:31–36

    Article  Google Scholar 

  17. Azizian J, Fallah-Bagher-Shaidaei H, Kefayati H (2003) A facile one-pot method for the preparation of N-alkyl isatins under microwave irradiation. Synth Commun 33:789–793

    Article  CAS  Google Scholar 

  18. Nikoofar K, Moazzez Dizgarani Sh (2015) HNO3@ nano SiO2: an efficient catalytic system for the synthesis of multi-substituted imidazoles under solvent-free conditions. J Suadi Chem Soc. https://doi.org/10.1016/j.jscs.2015.11.006

    Article  Google Scholar 

  19. Bergman J, Eklund N (1980) Synthesis and studies of tris-indolobenzenes and related compounds. Tetrahedron 36:1445–1450

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kobra Nikoofar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikoofar, K., Khalili, Z. HNO3@nano SiO2 Catalyzed Green and Efficient Synthesis of Symmetrical and Unsymmetrical Di(indolyl)indoline-2-ones by Stirring and Grindstone Methods. Natl. Acad. Sci. Lett. 41, 361–364 (2018). https://doi.org/10.1007/s40009-018-0710-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40009-018-0710-6

Keywords

Navigation