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Pentaerythritol as efficient H-bonding organocatalyst for synthesis of indazolo[2,1-b]phthalazine-trione derivatives

  • Shohreh Farahmand
  • Roya Ayazi-NasrabadiEmail author
  • Mohammad Mokhlesi
  • Mohammad Ali ZolfigolEmail author
Article
  • 45 Downloads

Abstract

Pentaerythritol was applied as an effective, biodegradable, nontoxic, mild, and commercially available H-bonding organocatalyst for synthesis of indazolo[2,1-b]phthalazine-trione derivatives via one-pot three-component condensation of aromatic aldehydes, phthalhydrazide, and dimedone under thermal solvent-free conditions in high to excellent yield.

Keywords

Biodegradable H-bonding organocatalyst Indazolo[2,1-b]phthalazine-triones Nontoxic Organocatalyst Pentaerythritol Solvent-free 

Notes

Acknowledgements

We thank Bu-Ali Sina University for financial support of our research group.

References

  1. 1.
    H. Pellissiera, Adv. Synth. Catal. 354, 237 (2012)CrossRefGoogle Scholar
  2. 2.
  3. 3.
    A. Moyano, R. Rios, Chem. Rev. 111, 4703 (2011)CrossRefGoogle Scholar
  4. 4.
    H. Kotsuki, H. Ikishima, A. Okuyama, Heterocycles 75, 757 (2008)CrossRefGoogle Scholar
  5. 5.
    D. Hack, P. Chauhan, S. Mahajan, D. Enders, Adv. Synth. Catal. 357, 253 (2015)CrossRefGoogle Scholar
  6. 6.
    M. Benaglia, S. Rossi, Org. Biomol. Chem. 8, 3824 (2010)CrossRefGoogle Scholar
  7. 7.
    M.S. Taylor, E.N. Jacobsen, Angew. Chem. Int. Ed. 45, 1520 (2006)CrossRefGoogle Scholar
  8. 8.
    A.G. Doyle, E.N. Jacobsen, Chem. Rev. 107, 5713 (2007)CrossRefGoogle Scholar
  9. 9.
    B. Atashkar, M.A. Zolfigol, S. Mallakpour, Mol. Cat. 452, 192 (2018)CrossRefGoogle Scholar
  10. 10.
    A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)CrossRefGoogle Scholar
  11. 11.
    A. Shaabani, A. Maleki, A. Hossein, Mol Divers. 15, 41 (2011)CrossRefGoogle Scholar
  12. 12.
    M. Shiri, Chem. Rev. 112, 3508 (2012)CrossRefGoogle Scholar
  13. 13.
    M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Chem. Rev. 110, 2250 (2010)CrossRefGoogle Scholar
  14. 14.
    A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)CrossRefGoogle Scholar
  15. 15.
    E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, 6234 (2011)CrossRefGoogle Scholar
  16. 16.
    P. Arora, V. Arora, H.S. Lamba, D. Wadhwa, Int. J. Pharm. Res. Sci. 3, 2947 (2012)Google Scholar
  17. 17.
    M.V. Reddy, G.C.S. Reddy, Y.T. Jeong, Tetrahedron 68, 6820 (2012)CrossRefGoogle Scholar
  18. 18.
    S. Grasso, G.D. Sarro, A.D. Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi, C.D. Micheli, J. Med. Chem. 1, 2851 (2000)CrossRefGoogle Scholar
  19. 19.
    A. Hashemzadeh, M.M. Amini, R. Tayebee, A. Sadeghian, L. Durndell, M.A. Isaacs, A. Osatiashtiani, C.M.A. Parlett, A.F. Lee, Mol. Catal. 440, 96 (2017)CrossRefGoogle Scholar
  20. 20.
    F. Kamali, F. Shirini, New J. Chem. 41, 11778 (2017)CrossRefGoogle Scholar
  21. 21.
    G. Turan-Zitouni, Z.A. Kaplancikli, K. Erol, F.S. Kilic, Farmaco 54, 218 (1999)CrossRefGoogle Scholar
  22. 22.
    K. Mazaahir, C. Ritika, J. Anwar, Chin. Sci. Bull. 57, 2273 (2012)CrossRefGoogle Scholar
  23. 23.
    M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)CrossRefGoogle Scholar
  24. 24.
    L. Nagarapu, R. Bantu, H.B. Mereyala, J. Heterocycl. Chem. 46, 728 (2009)CrossRefGoogle Scholar
  25. 25.
    H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A Gen. 345, 128 (2008)CrossRefGoogle Scholar
  26. 26.
    J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 7300 (2009)CrossRefGoogle Scholar
  27. 27.
    H.R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi, M. Ghashang, J. Iran. Chem. Res. 2, 57 (2009)Google Scholar
  28. 28.
    H.R. Shaterian, A. Hosseinian, M. Ghashang, ARKIVOC 2, 59 (2009)Google Scholar
  29. 29.
    X. Wang, W.W. Ma, L.Q. Wu, F.L. Yan, J. Chin. Chem. Soc. 11, 1341 (2010)CrossRefGoogle Scholar
  30. 30.
    X. Shi, J. Li, W. Zhong, J. Li, J. Chem. Res. 10, 17 (2012)CrossRefGoogle Scholar
  31. 31.
    M. Shekouhy, A. Hasaninejad, Ultrason. Sonochem. 19, 307 (2012)CrossRefGoogle Scholar
  32. 32.
    B.R. Madje, J.V. Bharad, M.B. Ubale, M.S. Shingare, Orbital Electron J. Chem. 4, 202 (2012)Google Scholar
  33. 33.
    A. Hasaninejed, M.R. Kazerooni, A. Zare, Catal. Today 196, 148 (2012)CrossRefGoogle Scholar
  34. 34.
    M. Kidwai, A. Jahan, R. Chauhan, N.K. Mishra, Tetrahedron Lett. 53, 1728 (2012)CrossRefGoogle Scholar
  35. 35.
    S.M. Sajadi, A.R. Faraji, S.A. Mahmud, F.J. Zeidali, Nat. Sci. Res. 2, 12 (2012)Google Scholar
  36. 36.
    A.V. Chate, P.K. Bhadke, M.A. Khande, J.N. Sangshetti, C.H. Gill, Chin. Chem. Lett. 28, 1577 (2017)CrossRefGoogle Scholar
  37. 37.
    A. Varghese, A. Nizam, R. Kulkarni, L. George, Eur. J. Chem. 4, 132 (2013)CrossRefGoogle Scholar
  38. 38.
    H.J. Wang, X.N. Zhang, Z.H. Zhang, Monatsh. Chem. 141, 425 (2010)CrossRefGoogle Scholar
  39. 39.
    R. Fazaeli, H. Aliyan, N. Fazaeli, Open Catal. J. 3, 14 (2010)CrossRefGoogle Scholar
  40. 40.
    M. Saha, S. Phukan, R. Jamatia, S. Mitra, A.K. Pal, RSC Adv. 3, 1714 (2013)CrossRefGoogle Scholar
  41. 41.
    H.R. Shaterian, F. Rigi, Starke 63, 340 (2011)CrossRefGoogle Scholar
  42. 42.
    R. Ghorbani-Vaghei, R. Karimi-Nami, Z. Toghraei-Semiromi, M. Amiri, M. Ghavidel, Tetrahedron 67, 1930 (2011)CrossRefGoogle Scholar
  43. 43.
    X. Zhang, H. Du, Z. Wang, Y.D. Wu, K. Ding, J. Org. Chem. 71, 2862 (2006)CrossRefGoogle Scholar
  44. 44.
    P. Ramamoorty, N. Krishnamurthy, Cryst. Res. Technol. 32, 525 (1997)CrossRefGoogle Scholar
  45. 45.
    P.G.N. Nayar, C.V. Raman, Proc. Ind. Acad. Sci. A 7, 251 (1938)CrossRefGoogle Scholar
  46. 46.
    M.E. Wilhelm, M.H. Anthofer, M. Cokoja, I.I.E. Markovits, W.A. Herrmann, F.E. Kuhn, ChemSusChem 7, 1357 (2014)CrossRefGoogle Scholar
  47. 47.
    M. Wang, J. Xu, H. Wu, S. Guo, Polym. Degrad. Stab. 91, 2101 (2006)CrossRefGoogle Scholar
  48. 48.
    X. Chen, Y. Chen, RSC Adv. 7, 31298 (2017)CrossRefGoogle Scholar
  49. 49.
    P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Curr. Org. Chem. 10, 2171 (2006)CrossRefGoogle Scholar
  50. 50.
    M. Zarei, E. Noroozizadeh, A.R. Moosavi-Zare, M.A. Zolfigol, J. Org. Chem. 83, 3645 (2018)CrossRefGoogle Scholar
  51. 51.
    M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, RSC Adv. 5, 71942 (2015)CrossRefGoogle Scholar
  52. 52.
    M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M.H. Beyzavie, R. Luque, Green Chem. 15, 2132 (2013)CrossRefGoogle Scholar
  53. 53.
    M.A. Zolfigol, F. Shirini, P. Salehi, M. Abedini, Curr. Org. Chem. 12, 183 (2008)CrossRefGoogle Scholar
  54. 54.
    O. Goli-Jolodar, F. Shirini, Theor. Exp. Chem. 52(6), 348 (2017)CrossRefGoogle Scholar
  55. 55.
    M.A. Zolfigol, M. Mokhlesi, S. Farahmand, J. Iran. Chem. Soc. 10, 577 (2013)CrossRefGoogle Scholar
  56. 56.
    M. Abedini, F. Shirini, J.M. Omran, J. Mol. Liq. 212, 405 (2015)CrossRefGoogle Scholar
  57. 57.
    A. Khazaei, M.A. Zolfigol, T. Faal-Rastegar, G. Chehardoli, S. Mallakpour, Iran. J. Catal. 3, 211 (2013)Google Scholar
  58. 58.
    H. Veisi, A. Sedrpoushan, A.R. Faraji, M. Heydari, S. Hemmati, B. Fatahi, RSC Adv. 5, 68523 (2015)CrossRefGoogle Scholar
  59. 59.
    A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A Chem. 373, 46 (2013)CrossRefGoogle Scholar
  60. 60.
    B. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res. Chem. Intermed. 41, 3675 (2015)CrossRefGoogle Scholar
  61. 61.
    S. Rostamnia, E. Doustkhah, Tetrahedron Lett. 55, 2508 (2014)CrossRefGoogle Scholar
  62. 62.
    G. Mohammadi Ziarani, N. Hosseini Mohtasham, N. Lashgari, A. Badiei, Res. Chem. Intermed. 41, 7581 (2015)CrossRefGoogle Scholar
  63. 63.
    B. Mirhosseini-Eshkevari, M.A. Ghasemzadeh, J. Safaei-Ghomi, Res. Chem. Intermed. 41, 7703 (2015)CrossRefGoogle Scholar
  64. 64.
    H.R. Shaterian, F. Rigi, Res. Chem. Intermed. 40, 1989 (2014)CrossRefGoogle Scholar
  65. 65.
    S.J. Saghanezhad, S. Sayyahi, Res. Chem. Intermed. 43, 2491 (2017)CrossRefGoogle Scholar
  66. 66.
    R. Mozafari, F. Heidarizadeh, Polyhedron 162, 263 (2019)CrossRefGoogle Scholar
  67. 67.
    M. Hamidinasab, A. Mobinikhaledi, ChemistrySelect 4, 17 (2019)CrossRefGoogle Scholar
  68. 68.
    M. Nikoorazm, A. Ghorbani-Choghamaranai, M. Khanmoradi, P. Moradi, J. Porous Mater. 25, 1831 (2018)CrossRefGoogle Scholar
  69. 69.
    M.A. Shaikh, M. Farooqui, S. Abed, Res. Chem. Intermed. 44, 5483 (2018)CrossRefGoogle Scholar
  70. 70.
    J. Albadi, M. Jalali, A. Momeni, Res. Chem. Intermed. 44, 2395 (2018)CrossRefGoogle Scholar
  71. 71.
    M. Esmaeilpour, J. Javidi, F. Dehghani, J. Iran. Chem. Soc. 13, 695 (2016)CrossRefGoogle Scholar
  72. 72.
    G. Sabitha, C. Srinivas, A. Raghavendar, J.S. Yadav, Helv. Chim. Acta 93, 1375 (2010)CrossRefGoogle Scholar
  73. 73.
    E. Mosaddegh, A. Hassankhani, Tetrahedron Lett. 52, 488 (2011)CrossRefGoogle Scholar
  74. 74.
    X.L. Xu, H.J. Zang, F. Yang, B.W. Cheng, Q.K. Wang, Y.L. Ren, Adv. Mater. Res. 332–334, 1884 (2011)Google Scholar
  75. 75.
    A.R. Kiasat, S. Noorizadeh, M. Ghahremani, S.J. Saghanejad, J. Mol. Struct. 1036, 216 (2013)CrossRefGoogle Scholar
  76. 76.
    R. Tayebee, M.M. Amini, S. Pouyamanesh, A. Aliakbari, Dalton Trans. 44, 5888 (2015)CrossRefGoogle Scholar
  77. 77.
    B. Afzalian, J.T. Mague, M. Mohamadi, S. Yousef Ebrahimipour, B. Pouramiri, E.T. Kermani, Cuihua Xuebao/Chin. J. Catal. 36, 1101 (2015)CrossRefGoogle Scholar
  78. 78.
    X.N. Zhao, G.F. Hu, M. Tang, T.T. Shi, X.L. Guo, T.T. Li, Z.H. Zhang, RSC Adv. 4, 51089 (2014)CrossRefGoogle Scholar
  79. 79.
    E. Mosaddegh, A. Hassankhani, Catal. Commun. 71, 65 (2015)CrossRefGoogle Scholar
  80. 80.
    C.S. Maheswari, C. Shanmugapriya, K. Revathy, A.J. Lalitha, Nanostruct. Chem. 7, 283 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryBu-Ali Sina UniversityHamadanIran

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