Trichloroisocyanuric Acid/NaNO₂ as a Novel Heterogeneous System for the N-Nitrosation of N,N-Dialkylamines Under Mild Conditions

Abstract

A combination of trichloroisocyanuric acid and sodium nitrite in the presence of wet SiO₂ was used as an effective nitrosating agent for the nitrosation of N,N-dialkyl amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.

Key words

trichloroisocyanuric acid - nitrosation - secondary amines - N-nitroso amines

References

• 1a Williams DLH. Nitrosation   Cambridge University Press; Cambridge: 1988.  p.77 
• 1b Williams DLH. Supplement F2, In The Chemistry of Amino, Nitroso, Nitro and Related Groups   John Wiley and Sons Ltd; New York: 1996.  p.665 
• 1c Keefer LK. Williams DLH. Methods in Nitric Oxide Reseach   John Wiley and Sons Ltd; New York: 1996.  p.509 ; and references cited therein
• 2 Garcia-Rio L. Leis JR. Moreira JA. Norberto F. J. Org. Chem.  2001,  66:  381 
• 3 Garcia-Rio L. Leis JR. Iglesias E. J. Org. Chem.  1997,  62:  4712 
• 4 Nudelman NS. Bonatti AE. Synlett  2000,  1825 ; and references cited therein
• 5 Olszewska T. Milewska MJ. Gdaniec M. Matuszynska H. Potonski T. J. Org. Chem.  2001,  66:  501 
• 6 Zolfigol MA. Shirini F. Ghorbani Choghamarani A. Taqian-nasab A. Keypour H. Salehzadeh S. J. Chem. Res., Synop.  2000,  420 
• 7 Rivera A. Gallo GI. Joseph-Nathan P. Synth. Commun.  1997,  27:  163 
• 8a Furniss B. S., Hannaford A. J., Smith P. W. G., Tatchell A. R.; Vogels Text Book of Practical Organic Chemistry; Longman: London and New York, 1989; 5th ed.:
• 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 
• 9 Castedo L. Riguera R. Vezquez MP. J. Chem. Soc., Chem. Commun.  1983,  301 
• 10 Fanning JC. Keefer LK. Larry K. J. Chem. Soc., Chem. Commun.  1987,  955 
• 11 Nakajima M. Warner JC. Anselme JP. Tetrahedron Lett.  1984,  25:  2619 
• 12 Chang SK. Hrrington GW. Rothstein M. Shergalis WA. Swern D. Vohra SK. Cancer Res.  1979,  39:  3871 
• 13 Makhova NN. Karpov GA. Mikhailyuk AN. Bova AE. KhmelŽnitskii LI. Novikov SS. Izv. Akad. Nauk SSSR, Ser. Khim.  1978,  1:  226 
• 14 Zolfigol MA. Synth. Commun.  1999,  29:  905 ; and references cited therein
• 15a Zolfigol MA. Ghorbani Choghamarani A. Shirini F. Keypour H. Salehzadeh S. Synth. Commun.  2001,  31:  359 
• 15b Zolfigol MA. Shirini F. Ghorbani Choghamarani A. Shiri A. Keypour H. Salehzadeh S. Asian J. Chem.  2001,  13:  849 
• 16 Zolfigol MA. Tetrahedron  2001,  57:  9509 ; and our references cited therein
• 17a Firouzabadi H. Iranpoor N. Hazarkhani H. Synlett  2001,  1641 ; and references cited therein
• 17b Xiog Z. Xuang NP. Zhong P. Synth. Commun.  2001,  31:  245 
• 18 Singer SS. Lijinsky W. Singer GM. Tetrahedron Lett.  1977,  19:  1613 
• 19 Singer SS. J. Org. Chem.  1978,  43:  4612 
• 20 Turnbull K. J. Heterocycl. Chem.  1985,  22:  965 
• 21 Richter-Addo GB. Acc. Chem. Res.  1999,  32:  529 
• 22 Zolfigol MA. Zebarjadian MH. Chehardoli GA. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem.  2001,  66:  3619 
• 23 Zolfigol MA. Zebarjadian MH. Sadeghi MM. Memarian HR. Mohammadpoor-Baltork I. Shamsipur M. Synth. Commun.  2001,  30:  929 
• 24 Zolfigol MA. Zebarjadian MH. Chehardoli G. Mallakpour SE. Shamsipur M. Tetrahedron  2001,  57:  1627