Issue

Vol. 26 No. 4 (2014): Vol 26 Issue 4

Copyright (c) 2014 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

New Heterocyclic Compounds From Butadienyl Sulfanes and Thiols

https://doi.org/10.14233/ajchem.2014.15720
Zeliha Gokmen
Division of Organic Chemistry, Department of Chemistry, Faculty of Engineering, Istanbul University, 34320, Avcilar, Istanbul, Turkey

Corresponding Author(s) : Zeliha Gokmen

gokm@istanbul.edu.tr

Asian Journal of Chemistry, Vol. 26 No. 4 (2014): Vol 26 Issue 4

Abstract

2-Chloroethyl-pentachlorobutadienyl-sulphide reacts with some heterocyclic thiols (7-mercapto-4-methylcoumarin, 2-mercaptobenzimidazole derivatives etc.) in water-ethanol mixture in the presence of sodium hydroxide to give the new heterocyclic thioethers. New 2-(4-(2-chloro-ethylthio)-1,2,3,4-tetrachlorobuta-1,3-dienylthio)ethanol compound was obtained from the reaction of 1,4-bis(2-hydroxyethylthio)-1,2,3,4-tetrachloro-1,3-butadiene with SOCl2 in pyridine. The structures of the new compounds were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, MS and fluorescence spectrophotometry.

Keywords

Thioethers Heterocyclic compounds Benzimidazole Coumarin Nicotinicacid Benzothiazole Fluorescence Property
Gokmen, Z. (2014). New Heterocyclic Compounds From Butadienyl Sulfanes and Thiols. Asian Journal of Chemistry, 26(4), 991–996. https://doi.org/10.14233/ajchem.2014.15720
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. T.T.-Y. Lee, Y. Kashiwada, L. Huang, J. Snider, M. Cosentino and K.-H. Lee, Bioorg. Med. Chem., 2, 1051 (1994); doi:10.1016/S0968-0896(00)82054-4.
  2. M. Itoigawa, C. Ito, H.T. Tan, M. Kuchide, H. Tokuda, H. Nishino and H. Furukawa, Cancer Lett., 169, 15 (2001); doi:10.1016/S0304-3835(01)00521-3.
  3. M. Campos-Toimil, F. Orallo, L. Santana and E. Uriarte, Bioorg. Med. Chem. Lett., 12, 783 (2002); doi:10.1016/S0960-894X(02)00015-X.
  4. A.A. Deana, G.E. Stokker, E.M. Schultz, R.L. Smith, E.J. Cragoe, H.F. Russo and L.S. Watson, J. Med. Chem., 26, 580 (1983); doi:10.1021/jm00358a023.
  5. S. Wawzoneck, Heterocycl. Compd., 2, 176 (1951).
  6. R. Fortin, Y. Girard, E. Grimm, J. Hutchinson and J. Scheigetz, US Patent 5424320 (1995).
  7. A.K. Sarkar, US Patent 3547952 (1970).
  8. T.B. Beamish and R. Dyllick, US Patent 5256336 (1993).
  9. B. Wang, X. Guan, Y. Hu and Z. Su, Polym. Adv. Technol., 18, 529 (2007); doi:10.1002/pat.911.
  10. W.W. Zhao and W.S. Bian, J. Mol. Struct. (Theochem), 859, 73 (2008); doi:10.1016/j.theochem.2008.03.004.
  11. M. Zimmerman, E. Yurewicz and G. Patel, Anal. Biochem., 70, 258 (1976); doi:10.1016/S0003-2697(76)80066-8.
  12. S.J. Hays, M.J. Rice, D.F. Ortwine, G. Johnson, R.D. Schwarz, D.K. Boyd, L.F. Copeland, M.G. Vartanian and P.A. Boxer, J. Pharm. Sci., 83, 1425 (1994); doi:10.1002/jps.2600831013.
  13. K. Aoki and A. Aikawa, US Patent 5962493 (1999).
  14. S.B. Seredenin, J.A. Blednov, V.L. Saveliev, T.Y. Mozhaeva, E.K. Orlova, K.S.O. Ragimov, M.A. Yarkova, G.G. Chichkanov, N.V. Kaverina, I.B. Tsorin, G.J. Kirsanova and G.G. Neznamov, U.S. Patent 6376666 (2002).
  15. L. Zirngibl, J. Fischer and K. Thiele, US Patent 4131608 (1977).
  16. U. Kraatz, B. Gallenkamp, A. Marhold, P. Wolfrum, W. Andersch, C. Erdelen, A. Turberg, O. Hansen and A. Harder, US Patent 6908937 (2005).
  17. U. Kraatz, B. Gallenkamp, A. Marhold, P. Wolfrum, W. Andersch, C. Erdelen, A. Turberg, O. Hansen and A. Harder, US Patent 6710045 (2004).
  18. A. Von Sprecher, W. Breitenstein, A. Beck, R.W. Lang and K. Oertle, US Patent 4785004 (1988).
  19. H.F. Campbell, D.E. Kuhla, W.L. Studt and S.A. Dodson, US Patent 4520025 (1985).
  20. Y. Lavat, US Patent 4766195 (1988).
  21. G. Cai and R.G. Gastinger, US Patent 5801290 (1988).
  22. W.L. Hawkins, V.L. Lanza, B.B. Loeffler, W. Matreyek and F.H. Winslow, J. Polym. Sci., 28, 439 (1958); doi:10.1002/pol.1958.1202811725.
  23. G.P. Stahyl, US Patent 4892965 (1990).
  24. V. Lamberti and H. Lemaire, US Patent 3988377 (1976).
  25. P.I. Pinko, E.I. Terakh, E.A. Gorokh, V.V. Nikulina, A.E. Prosenko and I.A. Grigor’ev, Russ. J. Appl. Chem., 75, 1660 (2002); doi:10.1023/A:1022288003999.
  26. A. Roedig, C. İbiş and G. Zaby, Chem. Ber., 114, 684 (1981); doi:10.1002/cber.19811140227.
  27. C. İbiş, Z. Gökmen and N.Y. Bozkurt, Phosphorus Sulfur Silicon Rel. Elem., 177, 2907 (2002); doi:10.1080/10426500214874.
  28. C. İbiş and Z. Gökmen, Phosphorus Sulfur Silicon Rel. Elem., 181, 939 (2006); doi:10.1080/10426500500272194.
  29. H. Bluestone, US Patent 3021370 (1962); Chem Abstr., 57, 3293c (1962).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0