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Horsetail plant (Equisetum arvense) and horsetail plant ash: application and comparison of their catalytic activities as novel and natural porous lewis acid catalysts for the one-pot green synthesis of 2-amino-4H-chromene derivatives under solvent-free conditions

  • Nina Hosseini Mohtasham
  • Mostafa GholizadehEmail author
Original Paper
  • 4 Downloads

Abstract

This study aims to use a new medicinal porous plant having a high content of silica known as horsetail and horsetail ash for the first time as novel, efficient, and environmentally friendly natural mild catalysts. The structure of these catalysts was characterized by different techniques such as FT-IR, XRF, SEM–EDS, N2 adsorption–desorption, XRD, and ICP analysis. The results obtained from the analysis revealed that both horsetail and horsetail ash could act as a solid acid catalyst. In addition, a further detailed analysis illustrated that they have a different surface area, porosity, and crystalline structure which can affect their catalytic activities. The synthesis of 2-amino-4H-chromene derivatives was performed via a one-pot three-component condensation of dimedone, malononitrile, and various aromatic aldehydes to compare their catalytic activities under solvent-free conditions. Due to its high porosity and high surface area, horsetail ash yields better results compared to the horsetail itself. FT-IR, mass, 1H-NMR, and 13C-NMR spectroscopies were used to identify the synthesized compounds in this study. An important advantage of this method is the use of these effective natural catalytic systems with characteristics such as low cost, mild reaction conditions, nontoxicity, and reusability which resulted in corresponding products in high to excellent yields and proper reaction times.

Keywords

Horsetail plant Ash Heterogeneous porous catalyst One-pot reaction 2-Amino-4H-chromene 

Notes

Acknowledgements

We are thankful to Ferdowsi University of Mashhad Research Council for financial support to this work (Grant No: 3/45801).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

13738_2019_1777_MOESM1_ESM.pdf (2.5 mb)
Supplementary material 1 (PDF 2543 kb)

References

  1. 1.
    R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)CrossRefGoogle Scholar
  2. 2.
    T.J.J. MŘller, R.V.A. Orru, V.A. Chebanov, Y.I. Sakhno, V.E. Saraev, E.A. Muravyova, A.Y. Andrushchenko, S.M. Desenko, V.R. Akhmetova, G.R. Khabibullina, Multi-component Reactions In Heterocyclic Chemistry (Springer, New York, 2011), pp. 31–73Google Scholar
  3. 3.
    K. Görlitzer, A. Dehne, E. Engler, Arch. Pharm. 316, 264 (1983)CrossRefGoogle Scholar
  4. 4.
    S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35, 3750 (1975)Google Scholar
  5. 5.
    T. Raj, R.K. Bhatia, R.K. Sharma, V. Gupta, D. Sharma, M.P.S. Ishar, Eur. J. Med. Chem. 44, 3209 (2009)CrossRefGoogle Scholar
  6. 6.
    P. Vats, V. Hadjimitova, K. Yoncheva, A. Kathuria, A. Sharma, K. Chand, A.J. Duraisamy, A.K. Sharma, A.K. Sharma, L. Saso, S.K. Sharma, Med. Chem. Res. 23, 4907 (2014)CrossRefGoogle Scholar
  7. 7.
    M.K. Manion, D. Hockenbery, Cancer Biol. Ther. 2, 104 (2003)CrossRefGoogle Scholar
  8. 8.
    Z.Q. Xu, K. Pupek, W.J. Suling, L. Enache, M.T. Flavin, Bioorg. Med. Chem. 14, 4610 (2006)CrossRefGoogle Scholar
  9. 9.
    E. Mosaddegh, A. Hassankhani, G. Mansouri, E.-J. Chem. 8, 529 (2011)CrossRefGoogle Scholar
  10. 10.
    A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)CrossRefGoogle Scholar
  11. 11.
    Y. Ren, W. Zhang, J. Lu, K. Gao, X. Liao, X. Chen, RSC Adv. 5, 79405 (2015)CrossRefGoogle Scholar
  12. 12.
    H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)CrossRefGoogle Scholar
  13. 13.
    M.R. Islami, E. Mosaddegh, Phosphorus Sulfur 184, 3134 (2009)CrossRefGoogle Scholar
  14. 14.
    X.-S. Wang, D.-Q. Shi, S.-J. Tu, C.-S. Yao, Synth. Commun. 33, 119 (2003)CrossRefGoogle Scholar
  15. 15.
    S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)CrossRefGoogle Scholar
  16. 16.
    S.-J. Tu, Y. Gao, C. Guo, D. Shi, Z. Lu, Synth. Commun. 32, 2137 (2002)CrossRefGoogle Scholar
  17. 17.
    I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)CrossRefGoogle Scholar
  18. 18.
    S. Tu, H. Jiang, Q. Zhuang, C. Miao, D. Shi, X. Wang, Y. Gao, Chin. J. Org. Chem. 23, 488 (2003)Google Scholar
  19. 19.
    O.H. Qareaghaj, S. Mashkouri, M.R. Naimi-Jamal, G. Kaupp, RSC Adv. 4, 48191 (2014)CrossRefGoogle Scholar
  20. 20.
    L. Sapei, Characterisation of silica in Equisetum hyemale and its transformation into biomorphous ceramics, pp. 1–158 (2007)Google Scholar
  21. 21.
    G. Holzhüter, K. Narayanan, T. Gerber, Anal. Bioanal. Chem. 376, 512 (2003)CrossRefGoogle Scholar
  22. 22.
    D. Cloutier, A.K. Watson, Weed Sci. 33, 358 (1985)CrossRefGoogle Scholar
  23. 23.
    F.H.M. Do Monte, J.G. dos Santos, M. Russi, V.M.N.B. Lanziotti, L.K.A.M. Leal, G.M. de Andrade Cunha, Pharmacol. Res. 49, 239 (2004)CrossRefGoogle Scholar
  24. 24.
    H. Oh, D.H. Kim, J.H. Cho, Y.C. Kim, J. Ethnopharmacol. 95, 421 (2004)CrossRefGoogle Scholar
  25. 25.
    H. Mekhfi, M. El Haouari, A. Legssyer, M. Bnouham, M. Aziz, F. Atmani, A. Remmal, A. Ziyyat, J. Ethnopharmacol. 94, 317 (2004)CrossRefGoogle Scholar
  26. 26.
    N.S. Sandhu, S. Kaur, D. Chopra, Asian J. Pharm. Clin. Res. 3, 146 (2010)Google Scholar
  27. 27.
    S. Soleimani, F.F. Azarbaizani, V. Nejati, Pak. J. Biol. Sci. 10, 4236 (2007)CrossRefGoogle Scholar
  28. 28.
    N. Radulović, G. Stojanović, R. Palić, Phytother. Res. 20, 85 (2006)CrossRefGoogle Scholar
  29. 29.
    M. Veit, C. Weidner, D. Strack, V. Wray, L. Witte, F.C. Czygan, Phytochemistry 31, 3483 (1992)CrossRefGoogle Scholar
  30. 30.
    A. Carnet, C. Petitjean-Freytet, D. Muller, J. Lamaison, Plants Med. Phytother. 25, 32 (1991)Google Scholar
  31. 31.
    J.G. dos Santos Junior, F.H.M. do Monte, M.M. Blanco, VMdNB Lanziotti, F.D. Maia, L.K. de Almeida Leal, Pharmacol. Biochem. Behav. 81, 593 (2005)CrossRefGoogle Scholar
  32. 32.
    M. Veit, K. Bauer, H. Geiger, F.C. Czygan, Planta Med. 58, 697 (1992)CrossRefGoogle Scholar
  33. 33.
    B. Fabre, B. Geay, P. Beaufils, Plantes Med. Phytother. 26, 190 (1993)Google Scholar
  34. 34.
    C. Beckert, C. Horn, J.P. Schnitzler, A. Lehning, W. Heller, M. Veit, Phytochemistry 44, 275 (1997)CrossRefGoogle Scholar
  35. 35.
    T. Řezanka, Phytochemistry 47, 1539 (1998)CrossRefGoogle Scholar
  36. 36.
    F. Adam, K. Kandasamy, S. Balakrishnan, J. Colloid Interface Sci. 304, 137 (2006)CrossRefGoogle Scholar
  37. 37.
    B.M. Cherian, L.A. Pothan, T. Nguyen-Chung, G. Mennig, M. Kottaisamy, S. Thomas, J. Agric. Food Chem. 56, 5617 (2008)CrossRefGoogle Scholar
  38. 38.
    X. Sun, F. Xu, R. Sun, P. Fowler, M. Baird, Carbohydr. Res. 340, 97 (2005)CrossRefGoogle Scholar
  39. 39.
    D. An, Y. Guo, Y. Zhu, Z. Wang, Chem. Eng. J. 162, 509 (2010)CrossRefGoogle Scholar
  40. 40.
    L. Sapei, N. Gierlinger, J. Hartmann, R. Nöske, P. Strauch, O. Paris, Anal. Bioanal. Chem. 389, 1249 (2007)CrossRefGoogle Scholar
  41. 41.
    P. Yuan, P.D. Southon, Z. Liu, M.E.R. Green, J.M. Hook, S.J. Antill, C.J. Kepert, J. Phys. Chem. C 112, 15742 (2008)CrossRefGoogle Scholar
  42. 42.
    M. Thommes, Chem. Ing. Tech. 82, 1059 (2010)CrossRefGoogle Scholar
  43. 43.
    N. Yalcin, V. Sevinc, Ceram. Int. 27, 219 (2001)CrossRefGoogle Scholar
  44. 44.
    M.G. Dekamin, M. Eslami, Green Chem. 16, 4914 (2014)CrossRefGoogle Scholar
  45. 45.
    M.A. Zolfigol, N. Bahrami-Nejad, F. Afsharnadery, S. Baghery, J. Mol. Liq. 221, 851 (2016)CrossRefGoogle Scholar
  46. 46.
    A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37, 69 (2013)CrossRefGoogle Scholar
  47. 47.
    S. Rostamnia, A. Nuri, H. Xin, A. Pourjavadi, S.H. Hosseini, Tetrahedron Lett. 54, 3344 (2013)CrossRefGoogle Scholar
  48. 48.
    S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37, 1097 (2007)CrossRefGoogle Scholar
  49. 49.
    R.-Y. Guo, Z.-M. An, L.-P. Mo, R.-Z. Wang, H.-X. Liu, S.-X. Wang, Z.-H. Zhang, ACS Comb. Sci. 15, 557 (2013)CrossRefGoogle Scholar
  50. 50.
    M.A. Zolfigol, M. Safaiee, N. Bahrami-Nejad, New J. Chem. 40, 5071 (2016)CrossRefGoogle Scholar
  51. 51.
    M. Amirnejad, M.R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh. Chem. 144, 1219 (2013)CrossRefGoogle Scholar
  52. 52.
    S. Gao, C.H. Tsai, C. Tseng, C.-F. Yao, Tetrahedron 64, 9143 (2008)CrossRefGoogle Scholar
  53. 53.
    P. Sharma, M. Gupta, R. Kant, V.K. Gupta, RSC Adv. 6, 32052 (2016)CrossRefGoogle Scholar
  54. 54.
    B. Sadeghi, A. Hassanabadi, S. Bidaki, J. Chem. Res. 35, 666 (2011)CrossRefGoogle Scholar
  55. 55.
    H. Naeimi, M. Farahnak Zarabi, Appl. Organomet. Chem. 32, e4225 (2018)CrossRefGoogle Scholar
  56. 56.
    S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C. R. Chim. 15, 394 (2012)CrossRefGoogle Scholar
  57. 57.
    S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)CrossRefGoogle Scholar
  58. 58.
    V. Safarifard, S. Beheshti, A. Morsali, CrystEngCommun 17, 1680 (2015)CrossRefGoogle Scholar
  59. 59.
    S. Pradhan, V. Sahu, B.G. Mishra, J. Mol. Catal. A Chem. 425, 297 (2016)CrossRefGoogle Scholar
  60. 60.
    A. Maleki, R. Ghalavand, R. Firouzi Haji, Appl. Organomet. Chem. 32, e3916 (2018)CrossRefGoogle Scholar
  61. 61.
    Y. Sarrafi, E. Mehrasbi, A. Vahid, M. Tajbakhsh, Chin. J. Catal. 33, 1486 (2012)CrossRefGoogle Scholar
  62. 62.
    K. Niknam, M. Khataminejad, F. Zeyaei, Tetrahedron Lett. 57, 361 (2016)CrossRefGoogle Scholar
  63. 63.
    A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A Gen. 402, 11 (2011)CrossRefGoogle Scholar
  64. 64.
    M. Abdollahi-Alibeik, F. Nezampour, React. Kinet. Mech. Catal. 108, 213 (2013)CrossRefGoogle Scholar
  65. 65.
    R.S. Bhosale, C.V. Magar, K.S. Solanke, S.B. Mane, S.S. Choudhary, R.P. Pawar, Synth. Commun. 37, 4353 (2007)CrossRefGoogle Scholar
  66. 66.
    B. Maleki, S.S. Ashrafi, RSC Adv. 4, 42873 (2014)CrossRefGoogle Scholar
  67. 67.
    D. Azarifar, S.M. Khatami, M.A. Zolfigol, R. Nejat-Yami, J. Iran. Chem. Soc. 11, 1223 (2014)CrossRefGoogle Scholar
  68. 68.
    R. Heydari, R. Rahimi, M. Kangani, A. Yazdani-Elah-Abadi, M. Lashkari, Acta Chem. Iasi 25, 163 (2017)CrossRefGoogle Scholar
  69. 69.
    A.A. Mohammadi, M.R. Asghariganjeh, A. Hadadzahmatkesh, Arab. J. Chem. 10, S2213 (2017)CrossRefGoogle Scholar
  70. 70.
    P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Tetrahedron Lett. 53, 4687 (2012)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceFerdowsi University of MashhadMashhadIran

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