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Microwave-assisted and scandium triflate catalyzed synthesis of tetrahydrobenzo[a]xanthen-11-ones

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Abstract

Synthesis of 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-ones was achieved by one-pot condensation of β-naphthol, substituted benzaldehydes, and 1,3-dicarbonyl compounds catalyzed by Sc(OTf)3 under microwave irradiation in excellent isolated yields. The catalyst was recycled up to four cycles with no appreciable loss in catalytic activity. The compounds were evaluated for Src kinase activity and anticancer activity.

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References

  1. Giri R, Goodell JR, Xing C, Benoit A, Kaur H, Hiasa H, Ferguson DM (2010) Bioorg Med Chem 18:1456

    Article  CAS  Google Scholar 

  2. Poupelin JP, Saint-Ruf G, Lacroix R (1978) Eur J Med Chem 13:381

    CAS  Google Scholar 

  3. El-Brashy AM, El-Sayed Metwally M, El-Sepai FA (2004) Farmaco 59:809

    Article  CAS  Google Scholar 

  4. Knight CG, Stephens T (1989) Biochem J 258:683

    CAS  Google Scholar 

  5. Gonçalves MST (2008) Chem Rev 109:190

    Article  Google Scholar 

  6. Ahmad M, King TA, Ko DK, Cha BH, Lee J (2002) J Phys D Appl Phys 35:1473

    Article  CAS  Google Scholar 

  7. Wawzonek S (1951) Xanthenes, xanthydrols and xanthylium salts. In: Elderfield RC (ed) Heterocyclic compounds, vol 2. Wiley, New York, p 419

    Google Scholar 

  8. Brimble MA, Gibson JS, Sperry J (2008) In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III. Elsevier, Oxford, p 419

  9. Bo E, Hillringhaus T, Nitsch J, Klussmann M (2011) Org Biomol Chem 9:1744

    Article  Google Scholar 

  10. Shinde PV, Kategaonkar AH, Shingate BB, Shingare MS (2011) Beilstein J Org Chem 7:53

    Article  CAS  Google Scholar 

  11. Gao S, Tsai CH, Yao CF (2009) Synlett 949

  12. Das B, Laxminarayana K, Krishnaiah M, Srinivas Y (2007) Synlett 3107

  13. Li J, Tang W, Lu L, Su W (2008) Tetrahedron Lett 49:7117

    Article  CAS  Google Scholar 

  14. Wang H-J, Ren X-Q, Zhang Y-Y, Zhang Z-H (2009) J Braz Chem Soc 20:1939

    Article  CAS  Google Scholar 

  15. Li J, Li J, Fang J, Su W (2010) Synth Commun 40:1029

    Article  CAS  Google Scholar 

  16. Khurana JM, Magoo D (2009) Tetrahedron Lett 50:4777

    Article  CAS  Google Scholar 

  17. Wang R-Z, Zhang L-F, Cui Z-S (2009) Synth Commun 39:2101

    Article  CAS  Google Scholar 

  18. Heravi M, Alinejhad H, Bakhtiari K, Oskooie H (2011) Mol Diver 15:239

  19. Zhang ZH, Zhang P, Yang SH, Wang HJ, Deng J (2010) J Chem Sci 122:427

    Article  CAS  Google Scholar 

  20. Zhang ZH, Wang HJ, Ren XQ, Zhang YY (2009) Monatsh Chem 140:1481

    Article  CAS  Google Scholar 

  21. Li J, Lu L, Su W (2010) Tetrahedron Lett 51:2434

    Article  CAS  Google Scholar 

  22. Larhed M, Moberg C, Hallberg A (2002) Acc Chem Res 35:717

    Article  CAS  Google Scholar 

  23. Kappe CO (2004) Angew Chem Int Ed 43:6250

    Article  CAS  Google Scholar 

  24. Roberts BA, Strauss CR (2005) Acc Chem Res 38:653

    Article  CAS  Google Scholar 

  25. Polshettiwar V, Varma RS (2008) Chem Soc Rev 37:1546

    Article  CAS  Google Scholar 

  26. Polshettiwar V, Varma RS (2008) Acc Chem Res 41:629

    Article  CAS  Google Scholar 

  27. Chauhan SMS, Sahoo BB, Srinivas KA (2001) Synth Commun 31:33

    Article  CAS  Google Scholar 

  28. Strauss CR, Rooney DW (2010) Green Chem 12:1340

    Article  CAS  Google Scholar 

  29. Caddick S, Fitzmaurice R (2009) Tetrahedron 65:3325

    Article  CAS  Google Scholar 

  30. Ju Y, Kumar D, Varma RS (2006) J Org Chem 71:6697

    Article  CAS  Google Scholar 

  31. Ju Y, Varma RS (2006) J Org Chem 71:135

    Article  CAS  Google Scholar 

  32. Paolini L, Petricci E, Corelli F, Botta M (2003) Synthesis 1039

  33. Sabitha G, Rao VRS, Sudhakar K, Kumar MR, Reddy EV, Yadav JS (2008) J Mol Catal A Chem 280:16

    Article  CAS  Google Scholar 

  34. Kobayashi S (1999) Eur J Org Chem 15

  35. Kobayashi S, Hachiya I (1994) J Org Chem 59:3590

    Article  CAS  Google Scholar 

  36. Kobayashi S, Sugiura M, Kitagawa H, Lam WWL (2002) Chem Rev 102:2227

    Article  CAS  Google Scholar 

  37. Chetia A, Saikia CJ, Lekhok KC, Boruah RC (2004) Tetrahedron Lett 45:2649

    Article  CAS  Google Scholar 

  38. Devi I, Bhuyan PJ (2004) Tetrahedron Lett 45:8625

    Article  CAS  Google Scholar 

  39. Trost BM (1995) Angew Chem Int Ed 34:259

    Article  CAS  Google Scholar 

  40. Wang L, Xia J, Qin F, Qian C, Sun J (2003) Synthesis 1241

  41. Weber L (2002) Curr Med Chem 9:2085

    CAS  Google Scholar 

  42. Van de Water RW, Pettus TRR (2002) Tetrahedron 58:5367

    Article  Google Scholar 

  43. Wolff A, Boehmer V, Vogt W, Ugozzoli F, Andreetti GD (1990) J Org Chem 55:5665

    Article  CAS  Google Scholar 

  44. Mashraqui SH, Paul MB, Mistry HD, Ghadigaonkar S, Meetsma A (2004) Chem Lett 33:1058

    Article  CAS  Google Scholar 

  45. Kumar A, Rao MS, Ahmad I, Khungar B (2009) Can J Chem 87:714

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank UGC New Delhi for financial support. MSR thanks BITS, Pilani for the institutional fellowships and US National Science Foundation, Grant Number CHE 0748555 and the American Cancer Society Grant # RSG-07-290-01-CDD for the financial support.

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Authors and Affiliations

  1. Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031, India

    Madharam Sudershan Rao & Anil Kumar

  2. Department of Biomedical and Pharmaceutical Sciences, University of Rhode Island, Kingston, RI, 02881, USA

    Bhupender S. Chhikara, Rakesh Tiwari, Amir N. Shirazi & Keykavous Parang

Authors
  1. Madharam Sudershan Rao
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  2. Bhupender S. Chhikara
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  3. Rakesh Tiwari
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  4. Amir N. Shirazi
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  5. Keykavous Parang
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  6. Anil Kumar
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Corresponding author

Correspondence to Anil Kumar.

Electronic supplementary material

Below is the link to the electronic supplementary material

706_2011_577_MOESM1_ESM.doc

Supplementary material containing experimental procedures for recovery and reuse of catalysts, cell culture, and cell proliferation assay, c-Src kinase activity assay, spectroscopic data and figures for 1H NMR, 13C NMR, and ESI–MS data for 4a–4s.

Supplementary material 1 (DOC 10349 kb)

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Rao, M.S., Chhikara, B.S., Tiwari, R. et al. Microwave-assisted and scandium triflate catalyzed synthesis of tetrahydrobenzo[a]xanthen-11-ones. Monatsh Chem 143, 263–268 (2012). https://doi.org/10.1007/s00706-011-0577-4

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  • DOI: https://doi.org/10.1007/s00706-011-0577-4

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