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Nanostructured coumarin-based cobalt complex as an efficient, heterogeneous and recyclable catalyst for the three-component synthesis of benzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives

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Abstract

An improved one-pot three-component reaction of carbonyl compounds (dimedon, 4-hydroxy coumarin and 1,3-cyclohexadion) with malononitrile and aryl aldehydes in aqueous media (H2O:EtOH) as a solvent with short reaction time for the synthesis of benzo[b]pyran and 3,4- dihydropyrano[c]chromane derivatives by using nanostructured coumarin-based cobalt complex as an efficient heterogeneous catalyst. The salient features of this new protocol include simple procedure, high yields, easy isolation of products without need to column chromatography and short reaction times. Also, the nanocatalyst was recovered by adding EtOH and reused five times without significant loss of its catalytic activity. Biological impact assessments of the complex were conducted by DNA cleavage ability assay and eukaryotic cell toxicity measurement. Although the complex showed single-strand DNA breakage under oxidative conditions, its high polar nature revealed a marked decrease in cell toxicity data due to the restriction on cell entry.

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References

  1. U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Tetrahedron Lett. 52, 5817 (2011)

    Article  CAS  Google Scholar 

  2. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    Article  CAS  Google Scholar 

  3. W.O. Foye, Prinicipi di Chemica Farmaceutica (Piccin, Padova, 1991), p. 416

    Google Scholar 

  4. M. Darbarwar, V. Sundaramurthy, Synthesis 1982, 337 (1982)

    Article  Google Scholar 

  5. A. Shaabani, M.M. Amini, S. Ghasemi, R. Ghadari, A.H. Rezayan, Y. Fazaeli, S. Feizi, Chem. Pharm. Bull. 58, 270 (2010)

    Article  CAS  Google Scholar 

  6. T.S. Jin, R.Q. Zhao, T.S. Li, Arkivoc 11, 176 (2006)

    Article  Google Scholar 

  7. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)

    Article  CAS  PubMed  Google Scholar 

  8. C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, PCT Int Appl WO 0075123, 2000 In Chem. Abstr. 134, 29313a (2001)

    Google Scholar 

  9. L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluor. Chem. 127, 97 (2006)

    Article  CAS  Google Scholar 

  10. X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139, 129 (2008)

    Article  CAS  Google Scholar 

  11. M. Beerappa, K. Shivashankar, RSC Adv. 5, 30364 (2015)

    Article  CAS  Google Scholar 

  12. O. Rosati, A. Pelosi, A. Temperini, V. Pace, M. Curini, Synthesis 48, 1533 (2016)

    Article  CAS  Google Scholar 

  13. P. Rai, A. Ibad, H. Sagir, I.R. Siddiqui, ChemistrySelect 1, 1300 (2016)

    Article  Google Scholar 

  14. N. Azizi, T.S. Ahooie, M.M. Hashemi, I. Yavari, Synlett 29, 645 (2018)

    Article  CAS  Google Scholar 

  15. S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64, 9143 (2008)

    Article  CAS  Google Scholar 

  16. A. Boumoud, A. Yahiaoui, T. Boumoud, A. Debache, J. Chem. Pharm. Res. 4, 795 (2012)

    CAS  Google Scholar 

  17. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  18. D.M. Pore, K.A. Undale, B.B. Dongare, U.V. Desai, Catal. letters 132, 104 (2009)

    Article  CAS  Google Scholar 

  19. D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu, H.W. Hu, Chinese. J. Org. Chem. 23, 877 (2003)

    CAS  Google Scholar 

  20. R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)

    Article  CAS  Google Scholar 

  21. S. Gurumurthi, V. Sundari, R. Valliappan, J. Chem. 6, S466 (2009)

    CAS  Google Scholar 

  22. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  23. D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagouda, R.S. Varma, Tetrahedron 63, 3093 (2007)

    Article  CAS  Google Scholar 

  24. A. Khalafi-Nezhad, M. Nourisefat, F. Panahi, Org. Biomol. Chem. 13, 7772 (2015)

    Article  CAS  PubMed  Google Scholar 

  25. Y.M. Litvinov, V.Y. Mortikov, A.M. Shestopalov, J. Comb. Chem. 10, 741 (2008)

    Article  CAS  PubMed  Google Scholar 

  26. H.R. Safaei, M. Shekouhy, A. Shirinfeshan, S. Rahmanpur, Mol. Divers. 16, 669 (2012)

    Article  CAS  PubMed  Google Scholar 

  27. H. Azizi, A. Khorshidi, K. Tabatabaeian, J. Iran. Chem. Soc. 15, 1023 (2018)

    Article  CAS  Google Scholar 

  28. A. Mulik, P. Hegade, S. Mulik, M. Deshmukh, Res. Chem. Intermed. 45, 5641 (2019)

    Article  CAS  Google Scholar 

  29. M.P. Lati, F. Shirini, M. Alinia-Asli, M.A. Rezvani, J. Nanosci. Nanotechnol. 20, 973 (2020)

    Article  CAS  PubMed  Google Scholar 

  30. H. Sharghi, M. Jokar, Heterocycles 71, 2721 (2007)

    Article  CAS  Google Scholar 

  31. K.B. Gudasi, M.S. Patil, R.S. Vadavi, Eur. J. Med. Chem. 43, 2436 (2008)

    Article  CAS  PubMed  Google Scholar 

  32. H. Sharghi, S.F. Razavi, M. Aberi, F. Tavakoli, M. Shekouhy, ChemistrySelect 5, 2662 (2020)

    Article  CAS  Google Scholar 

  33. M.G. Dekamin, M. Eslami, Green Chem. 16, 4914 (2014)

    Article  CAS  Google Scholar 

  34. M. Abdollahi-Alibeik, F. Nezampour, React. Kinet. Mech. Catal. 108, 213 (2013)

    Article  CAS  Google Scholar 

  35. H.R. Saadati-Moshtaghin, F.M. Zonoz, Mater. Chem. Phys. 199, 159 (2017)

    Article  CAS  Google Scholar 

  36. J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)

    Article  CAS  Google Scholar 

  37. M.A. Nasseri, S.M. Sadeghzadeh, J. Iran. Chem. Soc. 10, 1047 (2013)

    Article  CAS  Google Scholar 

  38. R. Nongrum, G.S. Nongthombam, M. Kharkongor, J. Rani, N. Rahman, C. Kathing, B. Myboh, R. Nongkhlaw, RSC Adv. 6, 108384 (2016)

    Article  CAS  Google Scholar 

  39. A. Gupte, R.J. Mumper, Cancer Treat. Rev. 35, 32 (2009)

    Article  CAS  PubMed  Google Scholar 

  40. F. Denizot, R. Lang, J. Immunol. Methods 89, 271 (1986)

    Article  CAS  PubMed  Google Scholar 

  41. J. Balou, M.A. Khalilzadeh, D. Zareyee, Sci. Rep. 9, 1 (2019)

    Article  CAS  Google Scholar 

  42. M.S. Mirhosseyni, F. Nemati, A. Elhampour, Comb. Chem. High. T Scr. 21, 87 (2018)

    Google Scholar 

  43. A. Maleki, Z. Hajizadeh, Silicon 11, 2789 (2019)

    Article  CAS  Google Scholar 

  44. M. Khoobi, L. Mamani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A: Chem. 359, 74 (2012)

    Article  CAS  Google Scholar 

  45. H. R. Saadati-Moshtaghin, F. Abbasinohoji, Polycyclic. Aromat. Compd. 1 (2019)

  46. M. Salimi, M.A. Nasseri, B.N. Jazi, J. Iran. Chem. Soc. 16, 2221 (2019)

    Article  CAS  Google Scholar 

  47. N.N. Pesyan, G.R. Bardajee, E. Kashani, M. Mohammadi, H. Batmani, Res. Chem. Intermed. 46, 347 (2020)

    Article  Google Scholar 

  48. A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Catal. Letters 104, 39 (2005)

    Article  CAS  Google Scholar 

  49. S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)

    Article  CAS  Google Scholar 

  50. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 7847 (2015)

    Article  CAS  Google Scholar 

  51. T.B. Kryston, A.B. Georgiev, P. Pissis, A.G. Georgakilas, Mutat. Res-Fund. Mol. M. 711, 193 (2011)

    Article  CAS  Google Scholar 

  52. L.F. Stadlmair, S. Grosse, T. Letzel, J.E. Drewes, J. Grassmann, Anal. Bioanal. Chem. 411, 339 (2019)

    Article  CAS  PubMed  Google Scholar 

  53. J.B. Wang, D.S. Cao, M.F. Zhu, Y.H. Yun, N. Xiao, Y.Z. Liang, J. Chemom. 29, 389 (2015)

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    Hashem Sharghi & Seyyede Faeze Razavi

  2. Department of Chemical and Materials Engineering, Faculty of Shahid Rajaee, Shiraz Branch, Technical and Vocational University (TVU), Shiraz, Iran

    Mahdi Aberi

  3. Molecular Biotechnology Laboratory, Department of Biology, Faculty of Science, Shiraz University, Shiraz, 71454, Iran

    Fatemeh Sabzalizadeh & Hamid Reza Karbalaei-Heidari

  4. Department of Chemistry, University of Manitoba, 144 Dysart Rd, 360 Parker Building, R3T 2N2, Winnipeg, MB, Canada

    Hamid Reza Karbalaei-Heidari

Authors
  1. Hashem Sharghi
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  2. Seyyede Faeze Razavi
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  3. Mahdi Aberi
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  4. Fatemeh Sabzalizadeh
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  5. Hamid Reza Karbalaei-Heidari
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Correspondence to Hashem Sharghi.

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Sharghi, H., Razavi, S.F., Aberi, M. et al. Nanostructured coumarin-based cobalt complex as an efficient, heterogeneous and recyclable catalyst for the three-component synthesis of benzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives. J IRAN CHEM SOC 18, 1641–1655 (2021). https://doi.org/10.1007/s13738-020-02136-1

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  • DOI: https://doi.org/10.1007/s13738-020-02136-1

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