Advertisement

Preparation, characterization and utilization of a novel dicationic molten salt as catalyst for the synthesis of bis(6-amino-1,3-dimethyluracil-5-yl)methanes

  • Abdolkarim ZareEmail author
  • Aysoda Ghobadpoor
  • Tayebeh Safdari
Article
  • 12 Downloads

Abstract

In this research, firstly, preparation and characterization of a novel dicationic molten salt, namely N,N,N′,N′-tetramethylethylenediaminium bisulfate ([TMEDA][HSO4]2), by 1H NMR, 13C NMR, FT-IR, mass, thermogravimetry, derivative thermogravimetry and differential thermal analysis data have been reported. Thereafter, utilization of [TMEDA][HSO4]2 as a recyclable catalyst for the solvent-free synthesis of bis(6-amino-1,3-dimethyluracil-5-yl)methanes via the reaction of 6-amino-1,3-dimethyluracil (2 eq.) and arylaldehydes (1 eq.) has been described.

Graphic abstract

Keywords

Dicationic molten salt N,N,N′,N′-Tetramethylethylenediaminium bisulfate ([TMEDA][HSO4]2Bis(6-amino-1,3-dimethyluracil-5-yl)methane 6-Amino-1,3-dimethyluracil Solvent free 

Notes

Acknowledgements

We thank the Research Council of Payame Noor University for the support of this work.

Supplementary material

11164_2019_4036_MOESM1_ESM.docx (1.6 mb)
Supplementary material 1 (DOCX 1627 kb)

References

  1. 1.
    M.A. Zolfigol, N. Bahrami-Nejad, S. Baghery, J. Mol. Liq. 558, 564 (2016)Google Scholar
  2. 2.
    M.A. Zolfigol, M. Yarie, S. Baghery, Synlett 27, 1418 (2016)CrossRefGoogle Scholar
  3. 3.
    M. Dashteh, S. Baghery, M.A. Zolfigol, Y. Bayat, A. Asgari, ChemistrySelect 4, 337 (2019)CrossRefGoogle Scholar
  4. 4.
    M.A. Zolfigol, S. Baghery, A.R. Moosavi-Zare, S.M. Vahdat, H. Alinezhad, M. Norouzi, RSC Adv. 5, 45027 (2015)CrossRefGoogle Scholar
  5. 5.
    S. Babaee, M.A. Zolfigol, M. Zarei, J. Zamanian, ChemistrySelect 3, 8947 (2018)CrossRefGoogle Scholar
  6. 6.
    M. Zarei, S.S. Sajadikhah, Res. Chem. Intermed. 42, 7005 (2016)CrossRefGoogle Scholar
  7. 7.
    P. Ren, S. Ci, Y. Ding, Z. Wen, Appl. Surf. Sci. 481, 1206 (2019)CrossRefGoogle Scholar
  8. 8.
    A. Rezaei, A.R. Kamali, Diam. Relat. Mater. 83, 146 (2018)CrossRefGoogle Scholar
  9. 9.
    G.H. Imanzadeh, A. Khalafi-Nezhad, A. Zare, A. Hasaninejad, A.R. Moosavi Zare, A. Parhami, J. Iran. Chem. Soc. 4, 229 (2007)CrossRefGoogle Scholar
  10. 10.
    A. Zare, A. Hasaninejad, M.H. Beyzavi, A. Parhami, A.R. Moosavi Zare, A. Khalafi-Nezhad, H. Sharghi, Can. J. Chem. 86, 317 (2008)CrossRefGoogle Scholar
  11. 11.
    L. Tian, J. Li, F. Liang, S. Chang, H. Zhang, M. Zhang, S. Zhang, J. Colloid Interface Sci. 536, 664 (2019)PubMedCrossRefGoogle Scholar
  12. 12.
    Z. Chen, Y. Gu, L. Hu, W. Xiao, X. Mao, H. Zhu, D. Wang, J. Mater. Chem. A 5, 20603 (2017)CrossRefGoogle Scholar
  13. 13.
    K. Du, R. Yu, M. Gao, Z. Chen, X. Mao, H. Zhu, D. Wang, Corros. Sci. 153, 12 (2019)CrossRefGoogle Scholar
  14. 14.
    W. Wang, Z. Wu, B. Li, B. Sundén, J. Therm. Anal. Calorim. 136, 1037 (2019)CrossRefGoogle Scholar
  15. 15.
    L.-L. Zoua, X. Chena, Y.-T. Wua, X. Wang, C.-F. Ma, Sol. Energy Mater. Sol. Cells 190, 12 (2019)CrossRefGoogle Scholar
  16. 16.
    M. Wang, Q. Tan, L. Liu, J. Li, ACS Sustain. Chem. Eng. 7, 8287 (2019)CrossRefGoogle Scholar
  17. 17.
    S. Liu, W. Han, B. Cui, X. Liu, F. Zhao, J. Stuart, S. Licht, J. Power Sources 342, 435 (2017)CrossRefGoogle Scholar
  18. 18.
    A. Zare, R. Khanivar, N. Irannejad-Gheshlaghchaei, M.H. Beyzavi, ChemistrySelect 4, 3953 (2019)CrossRefGoogle Scholar
  19. 19.
    K. Nikoofar, F. MolaeiYielzoleh, Res. Chem. Intermed. 44, 7353 (2018)CrossRefGoogle Scholar
  20. 20.
    A. Zare, A. Kohzadian, Z. Abshirini, S.S. Sajadikhah, J. Phipps, M. Benamarad, M.H. Beyzavi, New J. Chem. 43, 2247 (2019)CrossRefGoogle Scholar
  21. 21.
    A. Zare, M. Sadeghi-Takallo, M. Karami, A. Kohzadian, Res. Chem. Intermed. 45, 2999 (2019)CrossRefGoogle Scholar
  22. 22.
    M. Fathalla, C.M. Lawrence, N. Zhang, J.L. Sessler, J. Jayawickrama, Chem. Soc. Rev. 38, 1608 (2009)PubMedCrossRefGoogle Scholar
  23. 23.
    A.R. Dinner, G.M. Blackburn, M. Karplus, Nature 413, 752 (2001)PubMedCrossRefGoogle Scholar
  24. 24.
    V. Nair, G. Chi, Q. Shu, J. Julander, D.F. Smee, Bioorg. Med. Chem. Lett. 19, 1425 (2009)PubMedPubMedCentralCrossRefGoogle Scholar
  25. 25.
    J.A. Valderrama, P. Colonelli, D. Vásquez, M.F. González, J.A. Rodríguez, C. Theoduloz, Bioorg. Med. Chem. 16, 10172 (2008)PubMedCrossRefGoogle Scholar
  26. 26.
    A. Drabczynska, C.E. Muller, A. Schiedel, B. Schumacher, J. KarolaWojciechowska, A. Fruzinski, W. Zobnina, O. Yuzlenko, K. Kiec-Kononowicz, Bioorg. Med. Chem. 15, 6956 (2007)PubMedCrossRefGoogle Scholar
  27. 27.
    V.E. Semenov, A.D. Voloshina, E.M. Toroptzova, N.V. Kulik, V.V. Zobov, R.K. Giniyatullin, A.S. Mikhailov, A.E. Nikolaev, V.D. Akamsin, V.S. Reznik, Eur. J. Med. Chem. 41, 1093 (2006)PubMedCrossRefGoogle Scholar
  28. 28.
    K. Yagi, K. Akimoto, N. Mimori, T. Miyake, M. Kudo, K. Arai, S. Ishii, Pest Manag. Sci. 56, 65 (2000)CrossRefGoogle Scholar
  29. 29.
    G.Q. Lu, X.Y. Li, D. Wang, F.H. Meng, Eur. J. Med. Chem. 171, 282 (2019)PubMedCrossRefGoogle Scholar
  30. 30.
    L. Sun, X.-W. Chu, C.-M. Liu, L.-X. Sheng, Z.-X. Chen, K.-G. Cheng, Med. Chem. Res. (in press)Google Scholar
  31. 31.
    E. Lunt, C.G. Newton, in Comprehensive Heterocyclic Chemistry, vol. 3, ed. by A.R. Katritzky, C.W. Rees (Pergamon, Oxford, 1984)Google Scholar
  32. 32.
    I. Devi, P.J. Bhuyan, Tetrahedron Lett. 46, 5727 (2005)CrossRefGoogle Scholar
  33. 33.
    C. Zhi, Z.-Y. Long, J. Gambino, W.-C. Xu, N.C. Brown, M. Barnes, M. Butler, W. LaMarr, G.E. Wright, J. Med. Chem. 46, 2731 (2003)PubMedCrossRefGoogle Scholar
  34. 34.
    G. Mohammadi Ziarani, N. Hosseini Nasab, N. Lashgari, RSC Adv. 6, 38827 (2016)CrossRefGoogle Scholar
  35. 35.
    D. Shi, J. Shi, S. Rong, Chin. J. Chem. 28, 791 (2010)CrossRefGoogle Scholar
  36. 36.
    G. Brahmachari, B. Banerjee, RSC Adv. 5, 39263 (2015)CrossRefGoogle Scholar
  37. 37.
    S. Das, A. J. Thakur, Eur. J. Org. Chem. 2011, 2301 (2011)CrossRefGoogle Scholar
  38. 38.
    J. Azizian, M.R. Mohammadizadeh, F. Teimouri, A.A. Mohammadi, A.R. Karimi, Synth. Commun. 36, 3631 (2006)CrossRefGoogle Scholar
  39. 39.
    R. Bansal, R.S. Kumar, G. Kumar, S. Thota, S. Thamotharan, V. Parthasarathi, A. Linden, J. Heterocycl. Chem. 45, 1789 (2008)CrossRefGoogle Scholar
  40. 40.
    A.R. Karimi, Z. Dalirnasab, M. Karimi, F. Bagherian, Synthesis 45, 3300 (2013)CrossRefGoogle Scholar
  41. 41.
    B. Banerjee, G. Brahmachari, Curr. Organocatal. 3, 125 (2016)CrossRefGoogle Scholar
  42. 42.
    R. Khanivar, A. Zare, Z. Naturforsch. 73b, 635 (2018)CrossRefGoogle Scholar
  43. 43.
    N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44, 6253 (2018)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran

Personalised recommendations