DOI QR코드

DOI QR Code

Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as Efficient Reagents to Direct Oxidative Conversion of Thiols and Disulfide to Sulfonyl Chlorides

  • Veisi, Hojat (Chemistry Department, Payame Noor University) ;
  • Ghorbani-Vaghei, Ramin (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University) ;
  • Mahmoodi, Jafar (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University)
  • Received : 2011.07.06
  • Accepted : 2011.08.19
  • Published : 2011.10.20

Abstract

Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.

Keywords

References

  1. Dudutiene, V.; Baranauskiene Matulis, D. Bioorg. Med. Chem.Lett. 2007, 17, 3335. https://doi.org/10.1016/j.bmcl.2007.03.100
  2. Allison, B. D.; Phuong, V. K.; McAtee, L. C.; Rosen, M.; Morton, M.; Prendergast, C.; Barrett, T.; Lagaud, G.; Freedman, J.; Li, L.; Wu, X.; Venkatesan, H.; Pippel, M.; Woods, C.; Rizzolio, M. C.; Hack, M.; Hoey, K.; Deng, X.; King, C.; Shanley, N. P.; Rabinowitz, M. H. J. Med. Chem. 2006, 49, 6371. https://doi.org/10.1021/jm060590x
  3. Mathvink, R. J.; Barritta, A. M.; Candelore, M. R.; Cascieri, M. A.; Deng, L.; Tota, L.; Strader, C. D.; Wyvratt, M. J.; Fisher, M. J.; Weber, A. E. Bioorg. Med. Chem. Lett. 1999, 9, 1869. https://doi.org/10.1016/S0960-894X(99)00277-2
  4. Donner, P. L.; Xie, Q.; Pratt, J. K.; Maring, C. J.; Kati, W.; Jiang, W.; Liu, Y.; Koev, G.; Masse, S.; Montgomery, D.; Molla, A.; Kempf, D. L. Bioorg. Med. Chem. Lett. 2008, 18, 2735. https://doi.org/10.1016/j.bmcl.2008.02.064
  5. Hoyle, J. The Chemistry of Sulfonic Acids, Esters and their Derivatives, In The Chemistry of Functional Groups; Patai, S.; Rapport, Z., Eds.; John Wiley & Sons: New York, 1991, Chap. 10, 351.
  6. Tanaka, K. The Chemistry of Sulfonic Acids, Esters and their Derivatives, In The Chemistry of Functional Groups; Patai, S.; Rapport, Z., Eds.; John Wiley & Sons: New York, 1991, Chap. 11, 401.
  7. Moore, J. D.; Herpel, R. H.; Lichtsinn, J. R.; Flynn, D. L.; Hanson, P. R. Org. Lett. 2003, 5, 105. https://doi.org/10.1021/ol0270273
  8. Dubbaka, S. R.; Vogel, P. J. Am. Chem. Soc. 2003, 125, 15292. https://doi.org/10.1021/ja038328q
  9. Kværnø, L.; Werder, M.; Hauser, H.; Carreira, E. M. Org. Lett. 2005, 7, 1145.
  10. Lassalle, G.; Galtier, D.; Galli, F. European patent 643047, 1995.
  11. Lezina, O. M.; Kuchin, A. V.; Rubtsova, S. A. Russian patent 2289574, 2006.
  12. Watson, R. J.; Batty, D.; Baxter, A. D.; Hannah, D. R.; Owen, D. A.; Montana, J. G. Tetrahedron Lett. 2002, 43, 683. https://doi.org/10.1016/S0040-4039(01)02151-7
  13. Percec, V.; Bera, T. K.; De, B. B.; Sanai, Y.; Smith, J.; Holerca, M. N.; Barboiu, B.; Grubbs, B. B. B.; Frechet, J. M. J. J. Org. Chem. 2001, 66, 2104.
  14. Chen, Z.; Demuth, T. P., Jr.; Wireko, F. C. Bioorg. Med. Chem. Lett. 2002, 11, 2111.
  15. Gareau, Y.; Pellicelli, J.; Laliberte, S.; Gauvreau, D. Tetrahedron Lett. 2003, 44, 7821. https://doi.org/10.1016/j.tetlet.2003.08.073
  16. Blotny, G. Tetrahedron Lett. 2003, 44, 1499. https://doi.org/10.1016/S0040-4039(02)02853-8
  17. Meinzer, A.; Breckel, A.; Thaher, B. A.; Manicone, N.; Otto, H.- H. Helv. Chim. Acta 2004, 87, 90. https://doi.org/10.1002/hlca.200490021
  18. Nishiguchi, A.; Maeda, K.; Miki, S. Synthesis 2006, 4131.
  19. Bahrami, K.; Khodaei, M. M.; Soheilizad, M. Synlett. 2009, 2773.
  20. Bonke, J. D.; Amos, D. T.; Olson, S. J. Synth. Commun. 2007, 37, 2039. https://doi.org/10.1080/00397910701356942
  21. Ho, D. K. H.; Chan, L.; Hooper, A.; Brennan, P. E. Tetrahedron Lett. 2011, 52, 820. https://doi.org/10.1016/j.tetlet.2010.12.050
  22. Nishiguchi, A.; Maeda, K.; Miki, S. Synthesis 2006, 4131.
  23. Kvaerno, L.; Werder, M.; Hauser, B. A.; Carreira, E. M. Org. Lett. 2005, 7, 1145. https://doi.org/10.1021/ol0502127
  24. Meinzer, A.; Breckel, A.; Thaher, B. A.; Manicone, N.; Otto, H.- H. Helv. Chim. Acta 2004, 8(1), 90.
  25. Prakash, G. K. S.; Mathew, T.; Panja, C.; Olah, G. A. J. Org. Chem. 2007, 72, 5847. https://doi.org/10.1021/jo070907g
  26. Veisi, H. Synthesis 2010, 2631.
  27. Veisi, H. Tetrahedron Lett. 2010, 51, 2109. https://doi.org/10.1016/j.tetlet.2010.02.052
  28. Veisi, H.; Ghorbani-Vaghei, R. Tetrahedron 2010, 66, 7445. https://doi.org/10.1016/j.tet.2010.07.015
  29. Ghorbani-Vaghei, R.; Azarifar, D.; Maleki, B. Bull. Korean Chem. Soc. 2004, 25, 953. https://doi.org/10.5012/bkcs.2004.25.7.953

Cited by

  1. ChemInform Abstract: Poly(N,N′-dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N′,N′-Tetrachlorobenzene-1,3-disulfonamide as Efficient Reagents to Direct Oxidative Conversion of Thiols and Disulfide to Sulfonyl Chlorides. vol.43, pp.10, 2012, https://doi.org/10.1002/chin.201210072
  2. as an Efficient System for the Preparation of Alkyl Halides vol.34, pp.3, 2013, https://doi.org/10.5012/bkcs.2013.34.3.820
  3. Synthesis and anticancer activity of thiosubstituted purines vol.24, pp.7, 2015, https://doi.org/10.1007/s00044-015-1364-2
  4. The solvolysis mechanism of simple secondary tosylates in 50% aqueous TFE vol.29, pp.12, 2016, https://doi.org/10.1002/poc.3559
  5. Synthesis and biological evaluation of new series 1,4-dihydropyridines vol.42, pp.5, 2016, https://doi.org/10.1007/s11164-015-2310-0
  6. ]pyrazole] derivatives vol.54, pp.1, 2016, https://doi.org/10.1002/jhet.2605
  7. Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions vol.19, pp.9, 2017, https://doi.org/10.1039/C7GC00556C