Abstract
Melamine reacted with chlorosufonic acid (ClSO3H) to form a new sulfamic-type acid, 1,3,5-triazine-2,4,6-triyltrisulfamic acid (TTSA). Both nitrosation of secondary amines and oxidation of urazoles were accomplished by using TTSA/NaNO2 system under mild and heterogeneous conditions with good to excellent yields.
Similar content being viewed by others
References
Thottumkara A P, Bowsher M S and Vinod T K 2005 Org. Lett. 7 2933 and references cited therein
Tamhankar B V, Desai U V, Mane R B, Kalkarni P P and Wadgaonkar P P 2002 Synth. Commun. 32 3643
Narender N, Srinivasu P, Kalkarni S J and Raghavan K V Synth. Commun. 32 2319
Wang B 2005 Synlett. 1342 and references cited therein
Chehardoli G 2006 Synlett. 2154 and references cited therein
Zolfigol M A, Choghamarani A G, Shahamirian M, Safaiee M, Mohammadpoor-Baltork I, Mallakpour S E and Abdollahi-Alibeik M 2005 Tetrahedron Lett. 46 558
Zolfigol M A, Azarifar D, Mallakpour S E, Mohammadpoor-Baltork I, Forghaniha A, Maleki B and Abdollahi-Alibeik M 2006 Tetrahedron Lett. 47 833
Christoforou A, Nicolaou G and Elemes Y 2006 Tetrahedron Lett. 47 9211
Stickler J C and Pirkle W H J. Org. Chem. 31 3444
Read G and Rechardson N R 1996 J. Chem. Soc., Perkin Trans. 1 167
Mallakpour S E 1992 J. Chem. Ed. 69 238
Mallakpour S and Rafiee Z 2007 Synlett. 1255
Williams D L H 1996 The chemistry of amino, nitroso, nitro and related groups, Supplement F2 (New York: John Wiley & Sons Ltd.) p. 665
Keefer L K and Williams D L H 1996 Methods in nitric oxide research (New York: John Wiley & Sons Ltd.) p. 509
Williams D L H 2004 Nitrosation reactions and the chemistry of nitric oxide (Elsevier)
Garcia-Rio L, Leis J R, Moreira J A and Norberto F 2001 J. Org. Chem. 66 381
Garcia-Rio L, Leis J R and Iglesias E 1997 J. Org. Chem. 62 4712
Furniss B S, Hannaford A J and Smith P W G 1989 Vogels text book of practical organic chemistry, 5th edn (London: Longman)
Sheriner R L, Reynold T L, Fuson C, Curtin D Y and Morrill T C 1980 The Systematic Identification of organic compounds, 6th edn (New Jersey: John Wiley and Sons) p. 220
Castedo L, Riguera R and Vezquez M P 1983 J. Chem. Soc., Chem. Commun. 301
Fanning J C, Keefer L K and Larry K 1987 J. Chem. Soc., Chem. Commun. 955
Kolvari E, Ghorbani-Choghamarani A, Salehi P, Shirini F and Zolfigol M A 2007 J. Iran. Chem. Soc. 4 126
Nakajima M, Warner J C and Anselme J P Tetrahedron Lett. 25 2619
Chang S K, Harrington G W, Rothstein M, Shergalis W A, Swern D and Vohra S K 1979 Cancer Res. 39 3871
Zolfigol M A, Zebarjadian M H, Chehardoli G, Keypour H, Salehzadeh S and Shamsipur M 2001 J. Org. Chem. 66 3619
Salehi P, Zolfigol M A, Shirini F and Baghbanzadeh M 2006 Curr. Org. Chem. 10 2171
Shirini F, Zolfigol M A, Salehi P and Abedini M 2008 Curr. Org. Chem. 12 183
Zolfigol M A, Mohammadpoor-Baltork I and Shiri M 2008 J. Iran. Chem. Soc. 5 90
Bamoniri A, Mirjalili B F, Zolfigol M A and Mohammadpoor-Baltork I 2007 J. Iran. Chem. Soc. 4 332
Bamoniri A, Zolfigol M A, Mohammadpoor-Baltork I and Mirjalili B F 2006 J. Iran. Chem. Soc. 3 85
Niknam K, Zolfigol M A, Sadabadi T and Nejati A 2006 J. Iran. Chem. Soc. 3 318
Iranpoor N, Firouzabadi H and Pourali A R 2003 Synthesis 1591
Zolfigol M A, Bagherzadeh M, Mallakpour S, Chehardoli G, Ghorbani-Choghamarani A, Koukabi N, Dehghanian M and Doroudgar M 2007 J. Mol. Catal. A: Chem. 270 219
Zolfigol M A, Chehardoli G, Ghaemi E, Madrakian E, Zare R, Azadbakht T, Niknam K and Mallakpour S 2008 Monatsh. Chem. 139 261 and references cited therein
Zolfigol M A, Ghorbani-Vaghei R, Mallakpour S, Chehardoli G, Choghamarani A G and Yazdi H A 2006 Synthesis 1631
Niknam K and Zolfigol M A 2006 Synth. Commun. 36 2311 and references cited there in
Zolfigol M A, Shirini F, Choghamarani A G and Mohammadpoor-Baltork I 2002 Green Chem. 4 562
Zolfigol M A and Safaiee M, 2004 Synlett. 827
Zolfigol M A, Salehi P and Safaiee M 2006 Lett. Org. Chem. 3 153
Zolfigol M A, Bagherzadeh M, Niknam K, Shirini F, Mohammadpoor-Baltork I, Choghamarani A G and Baghbanzadeh M 2006 J. Iran. Chem. Soc. 3 73
Zolfigol M A, Chehardoli G, Salehzadeh S, Adams H and Ward M D 2007 Tetrahedron Lett. 48 7969
Zolfigol M A, Bagherzadeh M, Mallakpour S, Chehardoli G, Kolvari E, Ghorbani-Choghamrani A and Koukabi N 2007 Catal. Commun. 8 256
Niknam K and Zolfigol M A 2006 J. Iran. Chem. Soc. 3 59
Zolfigol M A, Ghorbani-Choghamarani A and Hazarkhani H 2002 Synlett. 1002
Zolfigol M A, Ghorbani-Choghamarani A, Taqian-Nasab A, Keypour H and Salehzadeh S 2003 Bull. Korean Chem. Soc. 24 638
Zolfigol M A, Shirini F and Ghorbani-Choghamarani A 2002 Synth. Commun. 32 1809
Zolfigol M A, Shirini F, Ghorbani-Choghamarani A, Shiri A, Keypour H and Salehzadeh S 2001 Synth. Commun. 31 359
Zolfigol M A and Bamoniri A 2002 Synlett. 1621
Zolfigol M A, Habibi D, Mirjalili B F and Bamoniri A 2003 Tetrahedron Lett. 44 3345
Itoh T, Matsuya Y, Maeta H, Miyazaki M, Nagata K and Ohsawa A Chem. Pharm. Bull. 47 819
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Chehardoli, G., Zolfigol, M.A., Faal-Rastegar, T. et al. 1,3,5-Triazine-2,4,6-triyltrisulfamic acid (TTSA): A new organic solid acid for the nitrosation of secondary amines and oxidation of urazoles in the presence of NaNO2 under mild and heterogeneous conditions. J Chem Sci 121, 441–447 (2009). https://doi.org/10.1007/s12039-009-0052-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-009-0052-5