Advertisement

Preparation and application of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide as new efficient ionic liquid catalyst for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives

  • Samira Karami
  • Ahmad Reza MomeniEmail author
  • Jalal Albadi
Article
  • 16 Downloads

Abstract

We report synthesis of triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide ([TPPHSP]Br) as a reusable green Brønsted-acidic ionic liquid catalyst and its application for synthesis of 5-arylidene barbituric acids and pyrano[2,3-d]pyrimidine derivatives by condensation reaction between aromatic aldehydes and barbituric acid or aromatic aldehydes, malononitrile, and barbituric acid in EtOH–H2O in reflux condition with good to excellent yield. The [TPPHSP]Br IL catalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), and thermogravimetric (TG) analysis and showed good catalytic activity and reusability.

Keywords

Triphenyl(propyl-3-hydrogen sulfate)phosphonium bromide Brønsted-acidic ionic liquid Phosphonium ionic liquid Pyrano[2,3-d]pyrimidines 5-Arylidene barbituric acids 

Notes

Acknowledgements

We are grateful to the Research Council of Shahrekord University for support of this research. The authors would like to thank Dr. Heshmat A. Samimi for reading this manuscript and giving helpful assistance.

Supplementary material

11164_2019_3798_MOESM1_ESM.pdf (1.3 mb)
Supplementary material 1 (PDF 1384 kb)

References

  1. 1.
    H.O. Bourbigou, L. Magna, D. Morvan, Appl. Catal. A Gen. 373, 1 (2010)CrossRefGoogle Scholar
  2. 2.
    J. Pavlinac, M. Zupan, K.K. Laali, S. Stavber, Tetrahedron 65, 5625 (2009)CrossRefGoogle Scholar
  3. 3.
    B.C. Ranu, S. Banerjee, Org. Lett. 7, 3049 (2005)CrossRefGoogle Scholar
  4. 4.
    T. Joseph, S. Sahoo, S.B. Halligudi, J. Mol. Catal. A Chem. 234, 107 (2005)CrossRefGoogle Scholar
  5. 5.
    D. Saha, A. Saha, B. Ranu, Tetrahedron Lett. 50, 6088 (2009)CrossRefGoogle Scholar
  6. 6.
    M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)CrossRefGoogle Scholar
  7. 7.
    A.K. Chakraborti, S.R. Roy, D. Kumar, P. Chopra, Green Chem. 10, 1111 (2008)CrossRefGoogle Scholar
  8. 8.
    P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis (Wiley-VCH, Weinheim, 2003)Google Scholar
  9. 9.
    J.D. Holbrey, R.D. Rogers, R.A. Mantz, P.C. Trulove, V.A. Cocalia, A.E. Visser, J.L. Anderson, J.L. Anthony, J.F. Brennecke, E.J. Maginn, T. Welton, Ionic Liquids in Synthesis (Wiley, Weinheim, 2008)Google Scholar
  10. 10.
    T. Welton, Coord. Chem. Rev. 248, 2459 (2004)CrossRefGoogle Scholar
  11. 11.
    C. Yue, A. Mao, Y. Wei, M. Lü, Catal. Commun. 9, 1571 (2008)CrossRefGoogle Scholar
  12. 12.
    S. Tang, G.A. Baker, H. Zhao, Chem. Soc. Rev. 41, 4030 (2012)CrossRefGoogle Scholar
  13. 13.
    M.M.A. Pereira, Curr. Org. Chem. 16, 1680 (2012)CrossRefGoogle Scholar
  14. 14.
    Q. Zhang, S. Zhang, Y. Deng, Green Chem. 13, 2619 (2011)CrossRefGoogle Scholar
  15. 15.
    F. Shirini, N.G. Khaligh, S. Akbari-dadamahaleh, J. Mol. Catal. A 365, 15 (2012)CrossRefGoogle Scholar
  16. 16.
    B.C. Ranu, L. Adak, S. Banerjee, Can. J. Chem. 85, 366 (2007)CrossRefGoogle Scholar
  17. 17.
    E.C. Taylor, R.J. Knopf, R.F. Meyer, A. Holmes, M.L. Hoefle, J. Am. Chem. Soc. 82, 5711 (1960)CrossRefGoogle Scholar
  18. 18.
    G. Heckmann, T. Bach, Angew. Chem. Int. Ed. 44, 1199 (2005)CrossRefGoogle Scholar
  19. 19.
    H. Xu, H. Tang, H. Feng, Y. Li, Eur. J. Med. Chem. 73, 46 (2014)CrossRefGoogle Scholar
  20. 20.
    F. Grams, H. Brandstetter, S. DAlò, D. Geppert, H.W. Krell, H. Lenert, V. Livi, E. Menta, A. Oliva, G. Zimmermann, Biol. Chem. 382, 1277 (2001)CrossRefGoogle Scholar
  21. 21.
    F.N.M. Naguib, D.L. Levesque, E.-C. Wang, R.P. Panzica, M.H.E. Kouni, Biochem. Pharmacol. 46, 1273 (1993)CrossRefGoogle Scholar
  22. 22.
    X. Chen, K. Tanaka, F. Yoneda, Chem. Pharm. 38, 307 (1990)CrossRefGoogle Scholar
  23. 23.
    H. Wamhoff, Adv. Heterocycl. Chem. 38, 229 (1985)CrossRefGoogle Scholar
  24. 24.
    J.A. Valderrama, P. Colonelli, D. Vásquez, M.F. González, J.A. Rodríguez, C. Theoduloz, Bioorgan. Med. Chem. 16, 10172 (2008)CrossRefGoogle Scholar
  25. 25.
    M. Nogueras, J. Cobo, M.L. Quijano, M. Melguizo, A. Sánchez, Nucleosides Nucleotides 13, 447 (1994)CrossRefGoogle Scholar
  26. 26.
    A.H. Shamroukh, M.E. Zaki, E.M. Morsy, F.M. Abdel-Motti, F.M. Abdel-Megeid, Arch. Pharm. (Weinh.) 340, 236 (2007)CrossRefGoogle Scholar
  27. 27.
    B.D. Dhorajiya, B.Z. Dholakiya, R.M. Mohareb, Med. Chem. Res. 23, 3941 (2014)CrossRefGoogle Scholar
  28. 28.
    A.S. Waghmare, S.S. Pandit, J. Saudi Chem. Soc. 21, 286 (2017)CrossRefGoogle Scholar
  29. 29.
    G. Thirupathi, M. Venkatanarayana, P.K. Dubey, Y.B. Kumari, Chem. Sci. Trans. 2, 441 (2013)CrossRefGoogle Scholar
  30. 30.
    J.M. Khurana, K. Vij, Catal. Lett. 138, 104 (2010)CrossRefGoogle Scholar
  31. 31.
    J.T. Li, M.X. Sun, Aust. J. Chem. 62, 353 (2009)CrossRefGoogle Scholar
  32. 32.
    J. Li, H. Dai, D. Liu, T. Li, Synth. Commun. 36, 789 (2006)CrossRefGoogle Scholar
  33. 33.
    X.Z. Chun Wang, J.J. Ma, X. Zhou, P.C. Zhi Wang, Y.J. Gao, Synth. Commun. 35, 2759 (2005)CrossRefGoogle Scholar
  34. 34.
    Y. Hu, Z.C. Chen, Z.G. Le, Synth. Commun. 34, 4521 (2004)CrossRefGoogle Scholar
  35. 35.
    Z. Ren, W. Cao, W. Tong, X. Jing, Synth. Commun. 32, 1947 (2002)CrossRefGoogle Scholar
  36. 36.
    N. Daneshvar, F. Shirini, M.S.N. Langarudi, R. Karimi-Chayjani, Bioorg. Chem. 77, 68 (2018)CrossRefGoogle Scholar
  37. 37.
    F. Shirini, M.S.N. Langarudi, N. Daneshvar, J. Mol. Liq. 234, 268 (2017)CrossRefGoogle Scholar
  38. 38.
    O.G. Jolodar, F. Shirini, M. Seddighi, Chin. J. Catal. 38, 1245 (2017)CrossRefGoogle Scholar
  39. 39.
    M. Bararjanian, S. Balalaie, B. Movassag, A.M. Amani, J. Iran. Chem. Soc. 6, 436 (2009)CrossRefGoogle Scholar
  40. 40.
    M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30, 273 (2016)CrossRefGoogle Scholar
  41. 41.
    B. Sabour, M. Peyrovi, M. Hajimohammadi, Res. Chem. Intermed. 41, 1343 (2015)CrossRefGoogle Scholar
  42. 42.
    N. Montazeri, Int. J. Nano Dimens. 6, 283 (2015)Google Scholar
  43. 43.
    A. Mobinikhaledi, N. Foroughifar, Inorg. Nano-Met. Chem. 40, 179 (2010)Google Scholar
  44. 44.
    O. Goli-Jolodar, F. Shirini, M. Seddighi, J. Iran. Chem. Soc. 13, 457 (2016)CrossRefGoogle Scholar
  45. 45.
    J. Albadi, A. Mansournezhad, T. Sadeghi, Res. Chem. Intermed. 41, 8317 (2015)CrossRefGoogle Scholar
  46. 46.
    A. Khazaei, H.A.A. Nik, A.R. Moosavi-Zare, J. Chin. Chem. Soc. 62, 675 (2015)CrossRefGoogle Scholar
  47. 47.
    D.N. Chavan, D.R. Patil, D.R. Kumbhar, M.B. Deshmukh, Chem. Sci. Rev. Lett. 4, 1051 (2015)Google Scholar
  48. 48.
    J. Yang, F. Mei, S. Fu, Y. Gu, Green Chem. 20, 1367 (2018)CrossRefGoogle Scholar
  49. 49.
    B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian J. 5, 2318 (2010)CrossRefGoogle Scholar
  50. 50.
    J.E. Biggs-Houck, A. Younai, J.T. Shaw, Curr. Opin. Chem. Biol. 14, 371 (2010)CrossRefGoogle Scholar
  51. 51.
    E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, 6234 (2011)CrossRefGoogle Scholar
  52. 52.
    A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M.M. Doroodmand, Appl. Catal. A Gen. 402, 11 (2011)CrossRefGoogle Scholar
  53. 53.
    J. Albadi, M. Jalali, A. Momeni, Res. Chem. Intermed. 44, 2395 (2018)CrossRefGoogle Scholar
  54. 54.
    J. Albadi, A. Momeni, A. Mansournezhad, Jordan J. Chem. 12, 233 (2017)Google Scholar
  55. 55.
    J. Albadi, A. Alihoseinzadeh, A. Razeghi, Catal. Commun. 49, 1 (2014)CrossRefGoogle Scholar
  56. 56.
    J. Albadi, J.A. Shrini, A. Mansournejhad, J. Chem. Sci. 126, 147 (2014)CrossRefGoogle Scholar
  57. 57.
    H. Tajik, I. Mohammadpoor-Baltork, J. Albadi, Synth. Commun. 37, 323 (2007)CrossRefGoogle Scholar
  58. 58.
    F. Shirini, M.A. Zolfigol, A.R. Aliakbar, J. Albadi, Synth. Commun. 40, 1022 (2010)CrossRefGoogle Scholar
  59. 59.
    W. Dai, Y. Zhang, Y. Tan, X. Luo, X. Tu, Appl. Catal. A Gen. 514, 43 (2016)CrossRefGoogle Scholar
  60. 60.
    P. Wasserscheid, M. Sesing, W. Korth, Green Chem. 4, 134 (2002)CrossRefGoogle Scholar
  61. 61.
    K. Qiao, C. Yokoyama, Catal. Commun. 7, 450 (2006)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Samira Karami
    • 1
  • Ahmad Reza Momeni
    • 1
    Email author
  • Jalal Albadi
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceShahrekord UniversityShahrekordIran

Personalised recommendations