Skip to main content
SpringerLink
Log in

Selective Synthesis of Bis(indolyl)methanes Under Solvent Free Condition Using Glucopyranosylamine Derived cis-Dioxo Mo(VI) Complex as an Efficient Catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

cis-Dioxomolybdenum(VI) complex of 4,6-O-ethylidene-β-d-glucopyranosylamine derived ligand has been used as an efficient catalyst in the selective synthesis of a series of bis(indolyl)methanes (BIMs) by condensing indole derivatives with carbonyl compounds. The adopted synthetic procedure is green in nature as solvent free reactions have been carried out using naturally occurring d-glucose derived ligands. Total 15 BIMs have been synthesised including four new ones, which have been characterized by mp, FTIR, NMR and mass spectroscopy. The catalyst has afforded good to excellent yield of BIMs in short reaction time and the former has been recycled five times without any significant loss in it’s catalytic efficiency.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2

Similar content being viewed by others

References

  1. Abdelbaqi K, Lack N, Guns ET, Kotha L, Safe S, Sanderson JT (2011) Prostate 71:1401

    Article  CAS  Google Scholar 

  2. Andey T, Patel A, Jackson T, Safe S, Singh M (2013) Eur J Pharm Sci 50:227

    Article  CAS  Google Scholar 

  3. Li X, Lee SO, Safe S (2012) Biochem Pharmacol 83:1445

    Article  CAS  Google Scholar 

  4. Rogan EG (2006) In vivo 20:221

    CAS  Google Scholar 

  5. Kobayashi M, Aoki S, Gato K, Matsunami K, Kurosu M, Kitagawa I (1994) Chem Pharm Bull 42:2449

    Article  CAS  Google Scholar 

  6. Sivaprasad G, Perumal PT, Prabavathy VR, Mathivanan N (2006) Bioorg Med Chem Lett 16:6302

    Article  CAS  Google Scholar 

  7. Sujatha K, Perumal PT, Muralidharan D, Rajendran M (2009) Indian J Chem 48B:267

    CAS  Google Scholar 

  8. Bao B, Sun Q, Yao X, Hong J, Lee CO, Sim CJ, Im KS, Jung JH (2005) J Nat Prod 68:711

    Article  CAS  Google Scholar 

  9. Casapullo A, Bifulco G, Bruno I, Riccio R (2000) J Nat Prod 63:447

    Article  CAS  Google Scholar 

  10. Garbe TR, Kobayashi M, Shimizu N, Takesue N, Ozawa M, Yukawa H (2000) J Nat Prod 63:596

    Article  CAS  Google Scholar 

  11. Mo LP, Ma ZC, Zhang ZH (2005) Synth Commun 35:1997

    Article  CAS  Google Scholar 

  12. Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959

    Article  CAS  Google Scholar 

  13. Zeng XF, Ji SJ, Wang SY (2005) Tetrahedron 61:10235

    Article  CAS  Google Scholar 

  14. Koshima H, Matsusaka W (2002) J Heterocycl Chem 39:1089

    Article  CAS  Google Scholar 

  15. Nagarajan R, Perumal PT (2002) Tetrahedron 58:1229

    Article  CAS  Google Scholar 

  16. Chatterjee A, Manna S, Banerji J, Pascard C, Prangé T, Shoolery JN (1980) J Chem Soc Perkin Trans 1:553

    Article  Google Scholar 

  17. Silveira CC, Mendes SR, Líbero FM, Lenardão EJ, Perin G (2009) Tetrahedron Lett 50:6060 (and Ref. cited there in)

    Article  CAS  Google Scholar 

  18. Mendes SR, Thurow S, Penteado F, Da Silva MS, Gariani RA, Perin G, Lenardão EJ (2015) Green Chem 17:4334

    Article  CAS  Google Scholar 

  19. Yadav JS, Reddy BVS, Sunitha S (2003) Adv Synth Catal 345:349

    Article  CAS  Google Scholar 

  20. Dhumaskar KL, Santosh GT (2012) Green Chem Lett Rev 5:353

    Article  CAS  Google Scholar 

  21. Hille R (1996) Chem Rev 96:2757

    Article  CAS  Google Scholar 

  22. Holm RH, Kennepohl P, Solomon EI (1996) Chem Rev 96:2239

    Article  CAS  Google Scholar 

  23. Grasselli RK (1999) Catal Today 49:141

    Article  CAS  Google Scholar 

  24. Jørgensen KA (1989) Chem Rev 89:431

    Article  Google Scholar 

  25. Schrock RR, Hoveyda AH (2003) Angew Chem Int Ed 42:4592

    Article  CAS  Google Scholar 

  26. Zhao J, Zhou X, Santos AM, Herdtweck E, Romão CC, Kühn FE (2003) Dalton Trans 19:3736

    Article  Google Scholar 

  27. Sah AK, Baig N (2015) Catal Lett 145:905

    Article  CAS  Google Scholar 

  28. Sah AK, Rao CP, Saarenketo PK, Wegelius EK, Kolehmainen E, Rissanen K (2001) Eur J Inorg Chem 11:2773

    Article  Google Scholar 

  29. Penieres-Carrillo G, Garcĺa-Estrada JG, Gutiérrez-Ramĺrez JL, Alvarez-Toledano C (2003) Green Chem 5:337

    Article  CAS  Google Scholar 

  30. Shirini F, Khaligh NG, Jolodar OG (2013) Dyes Pigm 98:290

    Article  CAS  Google Scholar 

  31. Ebrahimipour SY, Khabazadeh H, Castro J, Sheikhshoaie I, Crochet A, Fromm KM (2015) Inorg Chim Acta 427:52

    Article  CAS  Google Scholar 

  32. An LT, Ding FQ, Zou JP, Lu XH, Zhang LL (2007) Chin J Chem 25:822

    Article  CAS  Google Scholar 

  33. Heravi MM, Bakhtiari K, Fatehi A, Bamoharram FF (2008) Catal Commun 9:289

    Article  CAS  Google Scholar 

  34. Chatterjee PN, Maity AK, Mohapatra SS, Roy S (2013) Tetrahedron 69:2816

    Article  CAS  Google Scholar 

  35. Ekbote SS, Deshmukh KM, Qureshi ZS, Bhanage BM (2011) Green Chem Lett Rev 4:177

    Article  CAS  Google Scholar 

  36. Sharma DK, Tripathi AK, Sharma R, Chib R, ur Rasool R, Hussain A, Singh B, Goswami A, Khan IA, Mukherjee D (2014) Med Chem Res 23:1643

    Article  CAS  Google Scholar 

  37. Shi XL, Xing X, Lin H, Zhang W (2014) Adv Synth Catal 356:2349

    Article  CAS  Google Scholar 

  38. Mendes SR, Thurow S, Fortes MP, Penteado F, Lenardão EJ, Alves D, Perin G, Jacob RG (2012) Tetrahedron Lett 53:5402

    Article  CAS  Google Scholar 

Download references

Acknowledgments

A. K. Sah is grateful to the University Grants Commission (UGC) for the financial support under Major Research Project. We are also thankful to DST FIST and UGC SAP for their financial support in procuring the instruments and developing the research infrastructure.

Author information

Authors and Affiliations

  1. Department of Chemistry, Birla Institute of Technology and Science, Pilani Campus, Pilani, Rajasthan, 333 031, India

    Noorullah Baig, Ganesh M. Shelke, Anil Kumar & Ajay K. Sah

Authors
  1. Noorullah Baig
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ganesh M. Shelke
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anil Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ajay K. Sah
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ajay K. Sah.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1315 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baig, N., Shelke, G.M., Kumar, A. et al. Selective Synthesis of Bis(indolyl)methanes Under Solvent Free Condition Using Glucopyranosylamine Derived cis-Dioxo Mo(VI) Complex as an Efficient Catalyst. Catal Lett 146, 333–337 (2016). https://doi.org/10.1007/s10562-015-1648-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-015-1648-7

Keywords

Search

Navigation