Skip to main content
Log in

A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles in H2O under reflux conditions, in good yields, is described.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. P.A. Grieco (ed.), Organic Synthesis in Water (Blackie Academic and Professional, London, 1998)

    Google Scholar 

  2. C.J. Li, T.H. Chang, Organic Reactions in Aqueous Media (Wiley, New York, 1997)

    Google Scholar 

  3. C.J. Li, Chem. Rev. 105, 3095 (2005)

    Article  CAS  Google Scholar 

  4. M. Marinovich, B. Viviani, V. Capra, E. Corsini, L. Anselmi, G. D’Agostino, A.D. Nucci, M. Binaglia, M. Tonini, C.L. Galli, Chem. Res. Toxicol 15, 26 (2002)

    Article  CAS  Google Scholar 

  5. C. Len, A.S. Boulogne-Merlot, D. Postel, G. Ronco, P. Villa, C. Goubert, E. Jeufrault, B. Mathon, H. Simon, J. Agric. Food Chem. 44, 2856 (1996)

    Article  CAS  Google Scholar 

  6. A.Z. Halimehjani, K. Marjani, A. Ashouri, Green Chem. 12, 1306 (2010)

    Article  CAS  Google Scholar 

  7. A.R. Katrizky, S. Singh, P.P. Mahapatra, N. Clemense, K. Kirichenko, Arkivoc 9, 63 (2005)

    Google Scholar 

  8. X.L. Hou, Z.M. Ge, T.M. Wang, W. Guo, J.R. Cui, T.M. Cheng, C.S. Lai, R.T. Li, Bioorg. Med. Chem. Lett. 16, 4214 (2006)

    Article  CAS  Google Scholar 

  9. Z. Cai, W. Zhou, L. Sun, Bioorg. Med. Chem. 15, 7809 (2007)

    Article  CAS  Google Scholar 

  10. J. Kendall, G. Rewcastle, R. Frederick, C. Mawson, W. Denny, E. Marshall, B. Baguley, C. Chaussade, S. Jack-Son, P. Shepherd, Bioorg. Med. Chem. 15, 7677 (2007)

    Article  CAS  Google Scholar 

  11. Y. Kanda, T. Ashizawa, K. Kawashima, S. Ikeda, T. Tamaoki, Bioorg. Med. Chem. Lett. 13, 455 (2003)

    Article  CAS  Google Scholar 

  12. A. Tyrkov, N. Urlyapova, A. Daudova, Pharm. Chem. J. 40, 377 (2006)

    Article  CAS  Google Scholar 

  13. C. Jacob, Nat. Prod. Rep. 23, 851 (2006)

    Article  CAS  Google Scholar 

  14. X.Y. Wang, Z.J. Guo, Anti-Cancer Agents Med. Chem. 7, 19 (2007)

    Article  Google Scholar 

  15. T. Ariga, T. Seki, BioFactors 26, 93 (2006)

    Article  CAS  Google Scholar 

  16. A.R.H. Van-Zanten, M. Oudijk, M.K.E. Nohlmans-Paulssen, Y.G. Vander-Meer, A.R.J. Girbes, K.H. Polderman, Br. J. Clin. Pharmacol. 63, 100 (2007)

    Article  CAS  Google Scholar 

  17. L.S. Konstantinova, O.A. Rakitin, C.W. Rees, Chem. Rev. 104, 2617 (2004)

    Article  CAS  Google Scholar 

  18. O.A. Attanasi, L.D. Crescentini, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, G. Moscatelli, M.S. Behalo, Org. Lett. 11, 2265 (2009)

    Article  CAS  Google Scholar 

  19. F. Wang, S. Cai, Z. Wang, C. Xi, Org. Lett. 13, 3202 (2011)

    Article  CAS  Google Scholar 

  20. K. Tanaka, A. Wada, K. Noguchi, Org. Lett. 8, 907 (2006)

    Article  CAS  Google Scholar 

  21. K. Nakano, G. Tatsumi, K. Nozaki, J. Am. Chem. Soc. 129, 15116 (2007)

    Article  CAS  Google Scholar 

  22. A. Hagooly, S. Rozen, J. Org. Chem. 69, 8786 (2004)

    Article  CAS  Google Scholar 

  23. L. Shi, X. Liu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem. 76, 4200 (2011)

    Article  CAS  Google Scholar 

  24. J.L. Cui, Z.M. Ge, T.M. Cheng, R.T. Li, Synth. Commun. 33, 1969 (2003)

    Article  CAS  Google Scholar 

  25. N. Azizi, B. Pourhasan, F. Aryanasab, M.R. Saidi, Synlett 8, 1239 (2007)

    Google Scholar 

  26. I. Yavari, M. Sirouspour, S. Souri, Monatsh. Chem. 141, 49 (2010)

    Article  CAS  Google Scholar 

  27. C. Nitsche, C.D. Klein, Tetrahedron Lett. 53, 5197 (2012)

    Article  CAS  Google Scholar 

  28. I. Yavari, R. Hajinasiri, S.Z. Sayyed-Alangi, N. Iravani, Monatsh. Chem. 139, 1029 (2008)

    Article  CAS  Google Scholar 

  29. I. Yavari, S. Seyfi, Z. Hossaini, M. Sabbaghan, F. Shirgahi-Talari, Monatsh. Chem. 139, 1479 (2008)

    Article  CAS  Google Scholar 

  30. J. Safaei-Ghomi, F. Salimi, A. Ramazani, J. Chem. Sci. 125, 1087 (2013)

    Article  CAS  Google Scholar 

  31. R. Ghorbani-Vaghei, M. Amiri, H. Veisi, Bull. Korean Chem. Soc. 33, 4047 (2012)

    Article  CAS  Google Scholar 

  32. G.R. Bardajee, S. Sadraei, S.M. Taimoory, E. Abtin, Asian J. Biochem. Pharm. Res. 1, 178 (2011)

    CAS  Google Scholar 

  33. E. Ghabraie, H. Moghimi, S. Balalaie, M. Bararjanian, F. Rominger, H.R. Bijanzadeh, J. Iran Chem. Soc. 10, 725 (2013)

    Article  CAS  Google Scholar 

  34. A. Alizadeh, N. Zohreh, H. Sabahnoo, Z. Noaparast, Tetrahedron 67, 1709 (2011)

    Article  CAS  Google Scholar 

  35. H. Huang, Y. Li, J. Yang, J. Jia, Q. Ye, L. Han, J. Gao, Tetrahedron 69, 5221 (2013)

    Article  CAS  Google Scholar 

  36. I. Yavari, M. Sirouspour, S. Souri, Mol. Divers 14, 611 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are thankful to the Office of Graduate Studies of the Vali-e-Asr University of Rafsanjan for partial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hossein Mehrabi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mehrabi, H., Esfandiarpour, Z. A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water. J IRAN CHEM SOC 12, 2051–2055 (2015). https://doi.org/10.1007/s13738-015-0681-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-015-0681-1

Keywords

Navigation