PDF herunterladen
Synlett 2002(10): 1621-1624
DOI: 10.1055/s-2002-34230
LETTER
© Georg Thieme Verlag Stuttgart · New York

Silica Sulfuric Acid/NaNO2 as a Novel Heterogeneous System for the Chemoselective N-Nitrosation of Secondary Amines under Mild Conditions

Mohammad Ali Zolfigol*a, Abdolhamid Bamonirib
a Chemistry Department, College of Science, Bu-Ali Sina University, Hamadan, 65174, Iran
e-Mail: Zolfi@basu.ac.ir;
b Chemistry Department, College of Science, Kashan University, Kashan, 51167, Iran
Weitere Informationen

Publikationsverlauf

Received 29 July 2002
Publikationsdatum:
23. September 2002 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Neat chlorosulfonic acid reacts with silica gel to give silica sulfuric acid in which sulfuric acid is immobilized on the surface of silica gel via a covalent bond. A combination of silica sulfuric acid and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of secondary amines to their corresponding nitroso derivatives under mild and hetero­geneous conditions in excellent yields.

Key words

silica sulfuric acid - nitrosation - secondary amines - N-nitrosoamines

    References

  • 1a

    Williams D. L. H.; Nitrosation; Cambridge University Press: Cambridge, 1988; 77-149.

  • 1b

    Williams D. L. H.; Supplement F2: The Chemistry of Amino, Nitroso, Nitro and Related Groups; John Wiley & Sons Ltd.: New York, 1996; 665-682.

  • 1c Keefer LK. Williams DLH. Methods in Nitric Oxide Research   John Wiley & Sons Ltd.; New York: 1996.  p.509 ; and references cited therein
    Google Scholar
  • 2 Garcia-Rio L. Leis JR. Moreira JA. Norberto F. J. Org. Chem.  2001,  66:  381 
    CrossrefGoogle Scholar
  • 3 Garcia-Rio L. Leis JR. Iglesias E. J. Org. Chem.  1997,  62:  4712 
    CrossrefGoogle Scholar
  • 4 Nudelman NS. Bonatti AE. Synlett  2000,  1825 ; and references cited therein
    Artikel in Thieme ConnectGoogle Scholar
  • 5 Olszewska T. Milewska MJ. Gdaniec M. Matuszynska H. Potonski T. J. Org. Chem.  2001,  66:  501 
    CrossrefGoogle Scholar
  • 6 Zolfigol MA. Shirini F. Ghorbani-Choghamarani A. Taqian-nasab A. Keypour H. Salehzadeh S. J. Chem. Research, Synop.  2000,  420 
    Google Scholar
  • 7 Rivera A. Gallo GI. Joseph-Nathan P. Synth. Commun.  1997,  27:  163 
    Google Scholar
  • 8a Furniss BS. Hannaford AJ. Smith PWG. Tatchell AR. Vogels Text Book of Practical Organic Chemistry   5th ed.:  Longman; London/New York: 1989. 
    Google Scholar
  • 8b Sheriner RL. Reynold TL. Fuson C. Curtin DY. Morrill TC. The Systematic Identification of Organic Compounds   6th ed.:  John Wiley and Sons; New York: 1980.  p.220-223 
    Google Scholar
  • 9 Castedo L. Riguera R. Vezquez MP. J. Chem. Soc., Chem. Commun.  1983,  301 
    CrossrefGoogle Scholar
  • 10 Fanning JC. Keefer LK. Larry K. J. Chem. Soc., Chem. Commun.  1987,  955 
    CrossrefGoogle Scholar
  • 11 Nakajima M. Warner JC. Anselme JP. Tetrahedron Lett.  1984,  25:  2619 
    CrossrefGoogle Scholar
  • 12 Chang SK. Harrington GW. Rothstein M. Shergalis WA. Swern D. Vohra SK. Cancer Res.  1979,  39:  3871 
    Google Scholar
  • 13 Makhova NN. Karpov GA. Mikhailyuk AN. Bova AE. KhmelŽnitskii LI. Novikov SS. Izv. Akad. Nauk SSSR, Ser. Khim.  1978,  1:  226 
    Google Scholar
  • 14 Zolfigol MA. Synth. Commun.  1999,  29:  905 
    CrossrefGoogle Scholar
  • 15 Zolfigol MA. Ghorbani-Choghamarani A. Hazarkhani H. Synlett  2002,  1002 
    Artikel in Thieme ConnectGoogle Scholar
  • 16a Zolfigol MA. Tetrahedron  2001,  57:  9509 ; and references cited therein
    CrossrefGoogle Scholar
  • 16b Zolfigol MA. Torabi M. Mallakpour SE. Tetrahedron  2001,  57:  8381 
    CrossrefGoogle Scholar
  • 16c Shirin F. Zolfigol MA. Mallakpour B. Mallakpour SE. Hagipour A. Tetrahedron Lett.  2002,  43:  1555 
    CrossrefGoogle Scholar
  • 17 Riego JM. Sedin Z. Zaldivar JM. Marziano NC. Tortato C. Tetrahedron Lett.  1996,  37:  513 
    CrossrefGoogle Scholar
  • 18 Turro NJ. Tetrahedron  1987,  43:  1589 
    CrossrefGoogle Scholar
  • 19 Olah GA. Molhotra R. Narang SC. J. Org. Chem.  1978,  43:  4628 
    Google Scholar
  • 20 Singer SS. Lijinsky W. Singer GM. Tetrahedron Lett.  1977,  19:  1613 
    Google Scholar
  • 21 Singer SS. J. Org. Chem.  1978,  43:  4612 
    Google Scholar
  • 22 Turnbull K. J. Heterocycl. Chem.  1985,  22:  965 
    CrossrefGoogle Scholar
  • 23 Richter-Addo GB. Acc. Chem. Res.  1999,  32:  529 
    CrossrefGoogle Scholar
  • 24 Zolfigol MA. Zebarjadian MH. Chehardoli GA. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem.  2001,  66:  3619 
    CrossrefGoogle Scholar
  • 25 Zolfigol MA. Zebarjadian MH. Sadeghi MM. Memarian HR. Mohammadpoor-Baltork I. Shamsipur M. Synth. Commun.  2001,  30:  929 
    Google Scholar
  • 26 Zolfigol MA. Zebarjadian MH. Chehardoli G. Mallakpour SE. Shamsipur M. Tetrahedron  2001,  57:  1627 
    CrossrefGoogle Scholar