Advertisement

Research on Chemical Intermediates

, Volume 42, Issue 12, pp 8175–8183 | Cite as

Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

  • Javad Safari
  • Masoud Sadeghi
Article

Abstract

An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80 °C in DMSO medium. A plausible mechanism is proposed in which α-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.

Keywords

Montmorillonite-K10 2-Aminothiazole Thiourea Methylcarbonyls Iodine 

Notes

Acknowledgment

We gratefully acknowledge the financial support from the Research Council of the University of Kashan for supporting this work by Grant No. 256722/III.

References

  1. 1.
    N.G. Smirnova, I.V. Zavarzin, M.M. Krayushkin, Chem. Heterocycl. Compd. 42, 144 (2006)CrossRefGoogle Scholar
  2. 2.
    S. Ghaemmaghami, B.C.H. May, A.R. Renslo, S.B. Prusine, J. Virol. 84, 3408 (2010)CrossRefGoogle Scholar
  3. 3.
    M.A. Gouda, M.A. Berghot, E.A. Baz, W.S. Hamama, Med. Chem. Res. 21, 1062 (2012)CrossRefGoogle Scholar
  4. 4.
    T. Iino, N. Hashimoto, K. Sasaki, S. Ohyama, R. Yoshimoto, H. Hosaka, T. Hasegawa, M. Chiba, Y. Nagata, J. Eiki, T. Nishimura, Bioorg. Med. Chem. 17, 3800 (2009)CrossRefGoogle Scholar
  5. 5.
    N. Singh, S.K. Bhati, A. Kumar, Eur. J. Med. Chem. 43, 2597 (2008)CrossRefGoogle Scholar
  6. 6.
    B.F. Abdel-Wahab, H.A. Abdel-Aziz, E.M. Ahmed, Eur. J. Med. Chem. 44, 2632 (2009)CrossRefGoogle Scholar
  7. 7.
    I.S. Adagu, J. Antimicrob. Chemother. 49, 103 (2002)CrossRefGoogle Scholar
  8. 8.
    G. Aridoss, S. Amirthaganesan, M.S. Kim, J.T. Kim, Y.T. Jeong, Eur. J. Med. Chem. 44, 4199 (2009)CrossRefGoogle Scholar
  9. 9.
    M. Kodomari, T. Aoyama, Y. Suzuki, Tetrahedron Lett. 43, 1717 (2002)CrossRefGoogle Scholar
  10. 10.
    D. Zhua, J. Chena, H. Xiaoa, M. Liua, J. Dinga, H. Wu, Synth. Commun. 39, 2895 (2009)CrossRefGoogle Scholar
  11. 11.
    B. Chen, S. Guo, X. Guo, G. Zhang, Y. Yu, Org. Lett. 17, 4698 (2015)CrossRefGoogle Scholar
  12. 12.
    H. Singh, P. Singh, K. Deep, Tetrahedron 39, 1655 (1983)CrossRefGoogle Scholar
  13. 13.
    T. Aoyama, S. Murata, I. Arai, N.I. Araki, T. Takido, Y. Suzuki, M. Kodomari, Tetrahedron 62, 3201 (2006)CrossRefGoogle Scholar
  14. 14.
    E. Kocabas, A. Burak Sarıguney, A. Coskun, Heterocycles 81, 2849 (2010)CrossRefGoogle Scholar
  15. 15.
    T.J. Donohoe, M.A. Kabeshova, A.H. Rathia, I.E.D. Smith, Synlett 2010, 2956 (2010)Google Scholar
  16. 16.
    D. Kumar, N.M. Kumar, G. Patel, S. Gupta, R.S. Varma, Tetrahedron Lett. 52, 1983 (2011)CrossRefGoogle Scholar
  17. 17.
    J.S. Yadav, B.V.S. Reddy, Y.G. Rao, A.V. Narsaiah, Tetrahedron Lett. 49, 2381 (2008)CrossRefGoogle Scholar
  18. 18.
    S. Rostamizadeh, R. Aryan, H.R. Ghaieni, A.M. Amani, Monatshefte Chem. 139, 1241 (2008)CrossRefGoogle Scholar
  19. 19.
    Y.-P. Zhu, J.-J. Yuan, Q. Zhao, M. Lian, Q.-H. Gao, M.-C. Liu, Y. Yang, A.-X. Wu, Tetrahedron 68, 173 (2012)CrossRefGoogle Scholar
  20. 20.
    S.M. Ghodse, V.N. Telvekar, Tetrahedron Lett. 56, 472 (2015)CrossRefGoogle Scholar
  21. 21.
    J. Zhao, J. Xu, J. Chen, M. He, X. Wang, Tetrahedron 71, 539 (2015)CrossRefGoogle Scholar
  22. 22.
    T. Keshari, R. Kapoorr, L.D.S. Yadav, Tetrahedron Lett. 56, 5623 (2015)CrossRefGoogle Scholar
  23. 23.
    Z. Abedi-Jazini, Z. Zarnegar, M. Sadeghi, J. Nanopart. Res. 17, 495 (2015)CrossRefGoogle Scholar
  24. 24.
    B.S. Kumar, A. Dhakshinamoorthy, K. Pitchumani, Catal. Sci. Technol. 4, 2378 (2014)CrossRefGoogle Scholar
  25. 25.
    O. Marvi, L.Z. Fekri, M. Takhti, Russ. J. Gen. Chem. 84, 1837 (2014)CrossRefGoogle Scholar
  26. 26.
    R. Pagadala, P. Chidurala, V. Jetti, J.S. Meshram, S. Maddila, S.B. Jonnalagadda, J. Heterocycl. Chem. 52, 397 (2015)CrossRefGoogle Scholar
  27. 27.
    D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68, 5735 (2003)CrossRefGoogle Scholar
  28. 28.
    M. Jeganathan, A. Dhakshinamoorthy, K. Pitchumani, Tetrahedron Lett. 55, 1616 (2014)CrossRefGoogle Scholar
  29. 29.
    A. Jha, A.C. Garade, M. Shirai, C.V. Rode, Appl. Clay Sci. 74, 141 (2013)CrossRefGoogle Scholar
  30. 30.
    D. Suresha, A. Dhakshinamoorthya, K. Kanagaraja, K. Pitchumani, Tetrahedron Lett. 54, 6479 (2013)CrossRefGoogle Scholar
  31. 31.
    J. Safari, S. Gandomi-Ravandi, S. Shariat, J. Iran. Chem. Soc. (2016). doi: 10.1007/s13738-016-0866-2 Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  1. 1.Department of Organic ChemistryUniversity of KashanKashanIran

Personalised recommendations