Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A New and Facile Protocol for the Synthesis of Dithiocarbamate-linked 3,4-Dihydro-2H-pyran Using N-Halo Catalysts Under Mild Conditions Reaction

  • Ghorbani-Vaghei, Ramin (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali-Sina University) ;
  • Amiri, Mostafa (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali-Sina University) ;
  • Veisi, Hojat (Department of chemistry, Payame Noor University)
  • Received : 2012.08.11
  • Accepted : 2012.09.14
  • Published : 2012.12.20
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Abstract

A new and facile protocol for the synthesis of dithiocarabamate in EtOH/$H_2O$ is described. Reaction of aromatic and aliphatic amines with $CS_2$ and 3,4-dihydro-2H-pyran in the presence of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] and poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] gives the corresponding dithiocarbamates in good to high yields.

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References

  1. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998
  2. Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997
  3. Li, C. J. Chem. Rev. 2005, 105, 3095. https://doi.org/10.1021/cr030009u
  4. Marinovich, M.; Viviani, B.; Capra, V.; Corsini, E.; Anselmi, L.; D'Agostino, G.; Nucci, A. D.; Binaglia, M.; Tonini, M.; Galli, C. L. Chem. Res. Toxicol. 2002, 15, 26. https://doi.org/10.1021/tx015538c
  5. Len, C.; Boulogne-Merlot, A. S.; Postel, D.; Ronco, G.; Villa, P.; Goubert, C.; Jeufrault, E.; Mathon, B.; Simon, H. J. Agric. Food Chem. 1996, 44, 2856. https://doi.org/10.1021/jf950751y
  6. Halimehjani, A. Z.; Marjani, K.; Ashouri, A. Green Chem. 2010, 12, 1306. https://doi.org/10.1039/c004711b
  7. Katrizky, A. R.; Singh, S.; Mahapatra, P. P.; Clemense, N.; Kirichenko, K. ARKIVOC. 2005, 9, 63.
  8. Hou, X. L.; Ge, Z. M.; Wang, T. M.; Guo, W.; Cui, J. R.; Cheng, T. M.; Lai, C. S.; Li, R. T. Bioorg. Med. Chem. Lett. 2006, 16, 4214. https://doi.org/10.1016/j.bmcl.2006.05.085
  9. Hou, X.; Ge, Z.; Wang, T.; Guo, W.; Cui, J.; Cheng, T.; Lai, C.; Li, R. Bioorg. Med. Chem. Lett. 2006, 16, 4214. https://doi.org/10.1016/j.bmcl.2006.05.085
  10. Len, C.; Postel, D.; Ronco, G.; Villa, P.; Goubert, C.; Jeufrault, E.; Mathon, B.; Simon, H. J. Agric. Food. Chem. 1997, 45, 3. https://doi.org/10.1021/jf9607371
  11. Ronconi, L.; Marzano, C.; Zanello, P.; Corsini, M.; Miolo, G.; Macca, C.; Trevisan, A.; Fregona, D. J. Med. Chem. 2006, 49, 1648. https://doi.org/10.1021/jm0509288
  12. Cao, S.-L.; Feng, Y.-P.; Jiang, Y.-Y.; Liu, S.-Y.; Ding, G.- Y.; Li, R.-T. Bioorg. Med. Chem. Lett. 2005, 15, 1915. https://doi.org/10.1016/j.bmcl.2005.01.083
  13. Goel, A.; Mazur, S. J.; Fattah, R. J.; Hartman, T. L.; Turpin, J. A.; Huang, M.; Rice, W. G.; Appella, E.; Inman, J. K. Bioorg. Med. Chem. Lett. 2002, 12, 767. https://doi.org/10.1016/S0960-894X(02)00007-0
  14. Morf, P.; Raimondi, F.; Nothofer, H.-G.; Schnyder, B.; Yasuda, A.; Wessels, J. M.; Jung, T. A. Langmuir 2006, 22, 658. https://doi.org/10.1021/la052952u
  15. Bongar, B. P.; Sadavarte, V. S.; Uppalla, L. S. J. Chem. Res. 2004, 9, 450.
  16. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley Interscience: New York, 1999; p 484.
  17. Plyusnin, V. F.; Grivin, V. P.; Larionov, S. V. Coord. Chem. Rev. 1997, 159, 121. https://doi.org/10.1016/S0010-8545(96)01308-2
  18. Hidaka, S.; Funakoshi, T.; Shimada, H.; Tsuroka, M.; Kojima, S. J. Appl. Toxicol. 1995, 15, 267. https://doi.org/10.1002/jat.2550150407
  19. Fujii, S.; Yoshimura, T. Coord. Chem. Rev. 2000, 198, 89. https://doi.org/10.1016/S0010-8545(99)00196-4
  20. Cvek, B.; Dvorak, Z. T. Curr. Pharm. Des. 2007, 30, 3155.
  21. Mehta, G. R.; Liu, J.; Constantinou, A.; Thomas, F. C.; Hawthorne, M.; You, M.; Gerhauser, C.; Pezzuto, M. J.; Moon, C. R.; Moriarty, M. R. Carcinogenesis 1995, 16, 399. https://doi.org/10.1093/carcin/16.2.399
  22. Schonenberger, V. H.; Lippert, P. Pharmazie 1972, 27, 139.
  23. Walter, W.; Bode, K. D. Angew. Chem., Int. Ed. Engl. 1967, 6, 281. https://doi.org/10.1002/anie.196702811
  24. Garin, J.; Melandz, E.; Merchain, F. L.; Tejero, T.; Urid, S.; Ayestaron, J. Synthesis 1991, 147.
  25. Xia, S.; Wang, X.; Ge, Z.-M.; Cheng, T.-M.; Li, R.-T. Tetrahedron 2009, 65, 1005. https://doi.org/10.1016/j.tet.2008.11.084
  26. Ranu, B. C.; Saha, A.; Banerjee, S. Eur. J. Org. Chem. 2008, 519.
  27. Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055. https://doi.org/10.1016/S0040-4039(01)00132-0
  28. Guo, B.; Ge, Z.; Cheng, T.; Li, R. Synth. Commun. 2001, 31, 3021. https://doi.org/10.1081/SCC-100105674
  29. Ghorbani-Vaghei, R.; Jalili, H. Synthesis 2005, 4, 1099.
  30. Ghorbani-Vaghei, R.; Shahbazee, E.; Veisi, H. Mendeleev Commun. 2005, 204.
  31. Ghorbani-Vaghei, R.; Zolfigol, M. A.; Chegeny, M.; Veisi, H. Tetrahedron Lett. 2006, 44, 4505.
  32. Ghorbani-Vaghei, R.; Jalili, H. Synthesis 2005, 4, 1099.
  33. Ghorbani-Vaghei, R.; Shahbazee, E. J. Braz. Chem. Soc. 2005, 16, 644.
  34. Zolfigol, M. A.; Ghorbani-Vaghei, R.; Mallakpour, S.; Chehardoli, G.; Ghorbani-Choghamani, A.; Yazdi Hosain, A. Synthesis 2006, 10, 1631.
  35. Ghorbani-Vaghei, R.; Akbari-Dadamahaleh, S. Tetrahedron Lett. 2009, 50, 1055. https://doi.org/10.1016/j.tetlet.2008.12.076
  36. Ghorbani-Vaghei, R. Tetrahedron Lett. 2003, 44, 4529.
  37. Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H.; Dehghani-Firouzabadi, A. Mol. Div. 2010, 14, 84.
  38. Ghorbani-Vaghei, R.; Amiri, M.; Moshfeghifar, N.; Veisi, H.; Akbari-Dadamahaleh, S. J. Iran. Chem. Soc. 2009, 6, 454.
  39. Ghorbani-Vaghei, R.; Karimi-Nami, R.; Toghraei-Semiromi, Z.; Amiri, M.; Ghavidel, M. Tetrahedron 2011, 67, 1930. https://doi.org/10.1016/j.tet.2011.01.024
  40. Ghorbani-Vaghei, R.; Shahbazi, H.; Veisi, H. Tetrahedron Lett. 2012, 53, 2325. https://doi.org/10.1016/j.tetlet.2012.02.101
  41. Ghorbani-Vaghei, R.; Veisi, H. Tetrahedron 2010, 66, 4445.
  42. Ghorbani-Vaghei, R.; Veisi, H. Mol. Div. 2010, 14, 249. https://doi.org/10.1007/s11030-009-9169-1
  43. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Profession: London, 1998.
  44. Li, C. J.; Chang, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
  45. Li, C. J. Chem. Rev. 2005, 105, 3095. https://doi.org/10.1021/cr030009u

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