Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Chemoselective N-Benzenesulfonylation of Aliphatic Amines

  • Kim, Ho-Kyun (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Park, Yong-Dae (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Kim, Jeum-Jong (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Lee, Me-Ho (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Chung, Hyun-A (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Kweon, Deok-Heon (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Cho, Su-Dong (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University) ;
  • Yoon, Yong-Jin (Department of Chemistry and Research Institute of Life Sciences, Gyeongsang National University)
  • Published : 2003.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

Chemoselective N-benzenesulfonylation of aliphatic amines using 2-(4-nitrobenzenesulfonyl)-4,5-dichloropyridazin-3(2H)-one (2) gave the corresponding 4-nitrobenzenesulfonamides in good or excellent yield. This method is a simple, mild and general procedure for the chemoselective N-benzenesulfonylation of aliphatic amines.

Keywords

References

  1. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiely: New York, 1991; pp 379-386.
  2. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. https://doi.org/10.1016/0040-4039(95)01316-A
  3. Bhatt, U.; Mohamed, N.; Just, G.; Roberts, E.Tetrahedron Lett. 1997, 38, 3679. https://doi.org/10.1016/S0040-4039(97)00726-0
  4. Ibuka, T.; Mimura, N.;Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.;Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62,999. https://doi.org/10.1021/jo961760o
  5. Wuts, P. G. M.; Northuis, J. M. Tetrahedron Lett. 1998,39, 3889. https://doi.org/10.1016/S0040-4039(98)00684-4
  6. Weireb, S. M.; Demiko, D. M.; Lessen, T. A. Tetrahedron Lett.1986, 27, 2099. https://doi.org/10.1016/S0040-4039(00)84458-5
  7. Malgres, P. E.; See, M. M.; Askin, D.; Reider,P. J. Tetrahedron Lett. 1997, 38, 5253. https://doi.org/10.1016/S0040-4039(97)01157-X
  8. Sun, P.; Weinreb, S. M.;Shang, M. J. Org. Chem. 1997, 62, 8604. https://doi.org/10.1021/jo971455i
  9. Nihei, K.−I.; Kato,M. J.; Yamane, T.; Palma, M. S.; Konno, K. Synlett 2001, 1167.
  10. Fukuyama, T.; Cheung, M.; Jow, C. K.; Hidai, Y.; Kan, T.Tetrahedron Lett. 1997, 38, 5581.
  11. Silveira, C. C.; Bernard, C.R.; Braga, A. L.; Kaufman, T. S. Synlett 2002, 907.
  12. Kweon, D. H.; Kim, H. K.; Kim, J. J.; Chung, H.-A.; Lee, W. S.;Kim, S. K.; Yoon, Y. J. J. Heterocyclic Chem. 2002, 39,203. https://doi.org/10.1002/jhet.5570390129
  13. Kang, Y. J.; Chung, H.-A.; Kim, J. J.; Yoon, Y. J. Synthesis 2002,733.

Cited by

  1. Chemoselective N-Benzenesulfonylation of Aliphatic Amines. vol.35, pp.17, 2004, https://doi.org/10.1002/chin.200417058
  2. )-ones vol.42, pp.3, 2005, https://doi.org/10.1002/jhet.5570420302
  3. Preparation of O-Alkylhydroxamic Acids Using 2-Acylpyridazin-3(2H)-ones in Water vol.25, pp.8, 2003, https://doi.org/10.5012/bkcs.2004.25.8.1273
  4. Convenient Preparation of O ‐Alkylhydroxamic Acids Using 2‐Acylpyridazin‐3(2 H )‐ones vol.35, pp.5, 2003, https://doi.org/10.1081/scc-200050375
  5. Regiochemistry in Reaction of 4,5-Dichloro-2-cyanopyridazin-3(2H)-one with Nucleophiles vol.31, pp.4, 2003, https://doi.org/10.5012/bkcs.2010.31.04.1061
  6. Regiochemistry in Reaction of 4,5-Dichloro-2-cyanopyridazin-3(2H)-one with Nucleophiles vol.31, pp.4, 2003, https://doi.org/10.5012/bkcs.2010.31.04.1061
  7. ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters vol.351, pp.None, 2003, https://doi.org/10.1016/j.molcata.2011.09.010
  8. Recent Progress in the Chemistry of Pyridazinones for Functional Group Transformations vol.83, pp.1, 2003, https://doi.org/10.1021/acs.joc.7b02481