Advertisement

One-pot, multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives containing ferrocenyl

  • Yuting Liu
  • Yang DangEmail author
  • Dawei Yin
  • Xiaoming Yang
  • Lan Yang
  • Qian Zou
Article
  • 18 Downloads

Abstract

A novel series of 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidin- 2(1H)-ones has been synthesized by the Biginelli reaction between different substituted aromatic aldehydes, acetylferrocene and urea in the presence of boric acid as a catalyst. In addition, the effects of different conditions on the reaction were explored. The structures of all the target compounds were confirmed by FT-IR, 1H NMR, and 13C NMR.

Keywords

Ferrocene 3,4-Dihydropyrimidin-2(1H)-one Biginelli reaction Synthesis Boric acid 

Notes

Acknowledgements

The authors are indebted to Prof. Baojian Liu for his support and encouragement. The authors are thankful to Shaanxi University of Science & Technology for FT-IR spectroscopy and NMR spectroscopy.

References

  1. 1.
    R. Olinski, D. Gackowski, M. Cooke, s. Biochim. Biophys. Acta 1869(1), 29 (2018)Google Scholar
  2. 2.
    F.A.F. Ragab, S.M. Abou-Seri, S. Abdel-Aziz, a. Eur. J. Med. Chem. 138, 140 (2017)CrossRefGoogle Scholar
  3. 3.
    D. Kumarasamy, B.G. Roy, J. Rocha-Pereira, Bioorg. Med. Chem. Lett. 27(2), 139 (2017)CrossRefGoogle Scholar
  4. 4.
    A.M. Maharramov, M.A. Ramazanov, G.A. Guliyeva, J. Mol. Struct. 1141, 39 (2017)CrossRefGoogle Scholar
  5. 5.
    M. Sahu, N. Siddiqui, R. Iqbal, Bioorg. Chem. 74, 166 (2017)CrossRefGoogle Scholar
  6. 6.
    Q. Ren, X. Liu, Z. Luo, Bioorg. Med. Chem. 25(3), 1042 (2016)CrossRefGoogle Scholar
  7. 7.
    A. Manos-Turvey, H.A. Al-Ashtal, P.G. Needham, Bioorg. Med. Chem. Lett. 26(20), 5087 (2016)CrossRefGoogle Scholar
  8. 8.
    K. Singh, H. Kaur, K. Chibale, Eur. J. Med. Chem. 66, 314 (2013)CrossRefGoogle Scholar
  9. 9.
    F. Iftikhar, Y. Ali, F.A. Kiani, Bioorg. Chem. 74, 53 (2017)CrossRefGoogle Scholar
  10. 10.
    M. Teleb, F.X. Zhang, J. Huang, Bioorg. Med. Chem. 25(6), 1926 (2017)CrossRefGoogle Scholar
  11. 11.
    M. Teleb, F.X. Zhang, A.M. Farghaly, Tetrahedron Lett. 57(47), 5135 (2016)CrossRefGoogle Scholar
  12. 12.
    P. Singh, A. Singh, M.A. Quraishi, J. Taiwan Inst. Chem. Eng. 60(5), 588 (2016)CrossRefGoogle Scholar
  13. 13.
    A. Dhandapani, S. Manivarman, S. Subashchandrabose, J. Mol. Struct. 1127, 212 (2017)CrossRefGoogle Scholar
  14. 14.
    B.K. Banik, A.T. Reddy, A. Datta, Tetrahedron Lett. 48(41), 7392 (2007)CrossRefGoogle Scholar
  15. 15.
    B.J. Ahn, M.S. Gang, K. Chae, Ind. Eng. Chem. 14(3), 401 (2008)CrossRefGoogle Scholar
  16. 16.
    J.C. Rodríguez-Domínguez, B. Dan, G. Kirsch, Tetrahedron Lett. 48(33), 5777 (2007)CrossRefGoogle Scholar
  17. 17.
    N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor, J. Mol. Catal. A Chem. 271(1), 14 (2007)CrossRefGoogle Scholar
  18. 18.
    N. Ahmed, Lier. JEV. Tetrahedron Lett. 48(31), 5407 (2007)CrossRefGoogle Scholar
  19. 19.
    M. Wu, J. Yu, W. Zhao, J. Fluor Chem. 132, 155 (2011)CrossRefGoogle Scholar
  20. 20.
    Y. Yu, D. Liu, C. Luo, Bioorg. Med. Chem. Lett. 17(12), 3508 (2007)CrossRefGoogle Scholar
  21. 21.
    S.D. Salim, K.G. Akamanchi, Catal. Commun. 12(12), 1153 (2011)CrossRefGoogle Scholar
  22. 22.
    P.A. Solovyev, A.A. Fesenko, A.D. Shutalev, J. Fluor Chem. 182(25), 28 (2016)CrossRefGoogle Scholar
  23. 23.
    A.M. Abdou, S. Botros, R.A. Hassan, Tetrahedron 71(1), 139 (2015)CrossRefGoogle Scholar
  24. 24.
    M.A. Bigdeli, G. Gholami, E. Sheikhhosseini, Chin. Chem. Lett. 22(8), 903 (2011)CrossRefGoogle Scholar
  25. 25.
    P. Attri, R. Bhatia, J. Gaur, Arabian J. Chem. 10(2), 206 (2017)CrossRefGoogle Scholar
  26. 26.
    D. Elhamifar, F. Shojaeipoor, J. Mol. Catal. A Chem. 426, 198 (2017)CrossRefGoogle Scholar
  27. 27.
    D. Shobha, M.A. Chari, A. Mano, Tetrahedron 65(51), 10608 (2009)CrossRefGoogle Scholar
  28. 28.
    F. Zamani, S.M. Hosseini, S. Kianpour, Solid State Sci. 26(23), 139 (2013)CrossRefGoogle Scholar
  29. 29.
    S. Asghari, M. Tajbakhsh, B.J. Kenari, Chin. Chem. Lett. 22(2), 127 (2011)CrossRefGoogle Scholar
  30. 30.
    S. Moghaddas, A. Davoodnia, M.M. Heravi, Chin. J. Catal. 33(4), 706 (2012)CrossRefGoogle Scholar
  31. 31.
    R. Tayebee, M. Ghadamgahi, Arabian J. Chem. 10, S757 (2017)CrossRefGoogle Scholar
  32. 32.
    K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22(1), 69 (2011)CrossRefGoogle Scholar
  33. 33.
    G. Sivagamisundari, A.M. Pushpalatha, S.J. Ranee, Int. J. Sci. Eng. Technol. 3(7), 852 (2014)Google Scholar
  34. 34.
    F. Shirini, M. Abedini, R. Pourhasan-Kisomi, Chin. Chem. Lett. 45(1), 111 (2014)CrossRefGoogle Scholar
  35. 35.
    F. Heidarizadeh, E.R. Nezhad, S. Sajjadifar, Sci. Iran. 20(3), 561 (2013)Google Scholar
  36. 36.
    Z.B. Xie, N. Wang, W.X. Wu, J. Biotechnol. 170, 1 (2014)CrossRefGoogle Scholar
  37. 37.
    J. Pandey, N. Anand, R.P. Tripathi, Tetrahedron 65(45), 9350 (2009)CrossRefGoogle Scholar
  38. 38.
    M.A. Kolosov, O.G. Kulyk, M.J.K. Al-Ogaili, Tetrahedron Lett. 56(32), 4666 (2015)CrossRefGoogle Scholar
  39. 39.
    J. Banothu, S. Basavoju, R. Bavantula, Tetrahedron Lett. 55(1), 224 (2014)CrossRefGoogle Scholar
  40. 40.
    Y. Liu, H. Zhang, D. Yin, Res. Chem. Intermed. 41(6), 3793 (2015)CrossRefGoogle Scholar
  41. 41.
    Y. Liu, G. Lian, D. Yin, Spectrochim. Acta Part A 100(1), 131 (2013)CrossRefGoogle Scholar
  42. 42.
    Y. Liu, G. Lian, D. Yin, Res. Chem. Intermed. 38, 1043 (2012)CrossRefGoogle Scholar
  43. 43.
    Y. Liu, L. Feng, D. Yin, J. Chem. Soc. Pak. 34(3), 702 (2012)Google Scholar
  44. 44.
    Y. Liu, J. Sheng, D. Yin, J. Organomet. Chem. 856, 27 (2018)CrossRefGoogle Scholar
  45. 45.
    M. Tengfei, Y. Lei, L. Guoqiang, W. Yen, G. Yanzi, W. Jun, T. Lei, ACS Macro lett. 8(6), 639 (2019)CrossRefGoogle Scholar
  46. 46.
    A. Csámpai, A.Z. Györfi, G.I. Turos, P. Sohar, J. Organomet. Chem. 694(22), 3667 (2009)CrossRefGoogle Scholar
  47. 47.
    Y. Liu, H. Xin, D. Yin, J. Mol. Struct. 1157, 482 (2018)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Yuting Liu
    • 1
  • Yang Dang
    • 1
    Email author
  • Dawei Yin
    • 1
  • Xiaoming Yang
    • 1
  • Lan Yang
    • 1
  • Qian Zou
    • 1
  1. 1.Shaanxi Key Laboratory of Chemical Additives for IndustryShaanxi University of Science and TechnologyXi’anChina

Personalised recommendations