Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Selective N-Nitrosation of Amines, N-Alkylamides and N-Alkylureas by N2O4 Supported on Cross-Linked Polyvinylpyrrolidone (PVP-N2O4) Nasser Iranpoor*, Habib Firouzabadi*, Ali-Reza PouraliDepartment of Chemistry, Shiraz University, Shiraz 71454, Iran Fax: +98(711)2280926; e-Mail: iranpoor@chem.susc.ac.ir; firouzabadi@chem.susc.ac.ir.; Recommend Article Abstract Buy Article All articles of this category Abstract N2O4 was supported on the cross-linked polyvinylpyrrolidone (PVP) to afford a solid, stable and recyclable nitrosating agent. This reagent shows excellent selectivity for N-nitrosation of dialkyl amines in the presence of diaryl-, arylalkyl-, trialkylamines and also for secondary amides in dichloromethane at room temperature under mild and heterogeneous conditions. Also N-nitroso-N-alkyl amides can be selectively prepared in the presence of primary amides and N-phenylamides under similar reaction conditions. Selective N-nitrosation or dealkylation and N-nitrosation of tertiary amines can also be performed by this reagent. Key words N-nitrosation - amine - amide - urea - polyvinylpyrrolidone Full Text References References 1a Ignarro LJ. Angew. Chem. Int. Ed. 1999, 38: 1882 1b Murad F. Angew. Chem. Int. Ed. 1999, 38: 1856 1c Pfeiffer S. Mayer B. Hemmens B. Angew. Chem. Int. Ed. 1999, 38: 1714 2a Montague PR. Gancayco CD. Winn MJ. Marchase RB. Friedlander MJ. Science 1994, 263: 973 2b Kwon S. George SC. NITRIC OXIDE: Biology and Chemistry 1999, 3: 348 2c Feldmam PL. Griffith OW. Stuehr DJ. Chem. Eng. News 1993, 71(Dec. 20): 26 3 Feelisch M. Stamler JS. In Methods in Nitric Oxide Research Feelisch M. Stamler JS. Wiley; Chichester: 1996. Chap. 7. 4a Wang PG. Xian M. Tang X. Wu X. Wen Z. Cai T. Janczuk AJ. Chem. Rev. 2002, 102: 1091 4b Tanno M. Sueyoshi S. Miyata N. Umehara K. Chem. Pharm. Bull. 1997, 45: 595 4c Advances in Pharmacology Vol. 34: Ignarro L. Murard F. Academic Press; New York: 1995. p.1-516 4d Cheng J.-P. Xian M. Wang K. Zhu X. Yin Z. Wang PG. J. Am. Chem. Soc. 1998, 120: 10266 5a Loeppky RN. In N-Nitrosamines and Related N-Nitroso Compounds, American Chemical Society Symposium Series, 553 Loeppky RN. Michejda CJ. American Chemical Society; Washington DC: 1994. 5b DeRubertis FK. Craven PA. Science 1976, 193: 897 6a Guo Z. Xian M. Zhang W. McGill A. Wang PG. Bioorg. Med. Chem. 2001, 9: 99 6b Chemistry and Biology of N-Nitroso Compounds Lijinsky W. Cambridge University Press; Cambridge: 1992. 7a Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1975, 14: 15 7b Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1972, 11: 1101 7c Seebach D. Enders D. Chem. Ber. 1975, 108: 1293 7d Seebach D. Enders D. Angew. Chem., Int. Ed. Engl. 1972, 11: 1102 8 Jörgensen KA. El-Wassimy MTM. Lawesson S.-O. Tetrahedron 1983, 39: 469 9a Kostyukovskii YaL. Melamed DB. Russ. Chem. Rev. 1988, 57: 350 9b Dictionary of Organic Compounds on CD-ROM, Version 6:1 Chapman & Hall; London: 1998. 10 Gdaniec M. Milewska MJ. Polonski T. J. Org. Chem. 1995, 60: 7411 11 Garcia Rio L. Leis JR. Iglesias E. J. Org. Chem. 1997, 62: 4701 12 Williams DLH. Nitrosation Cambridge University Press; Cambridge: 1988. 13 Zolfigol MA. Zabarjadian MH. Chehardoli G. Keypour H. Salehzadeh S. Shamsipur M. J. Org. Chem. 2001, 66: 3619 14 Demir AS. Mahasneh AS. Aksoy H. Gercek Z. Synth. Commun. 1992, 22: 2607 15a Lovejoy DJ. Vosper AJ. J. Chem. Soc. (A) 1968, 2325 15b Casado J. Castro A. Ramon Leis J. Quintela MAL. Mosquera M. Monatsh. Chem. 1983, 114: 639 16a White EH. Feldman WR. J. Am. Chem. Soc. 1957, 79: 5832 16b Challis BC. Kyrtopoulos SA. J. Chem. Soc. Perkin Trans. 2 1978, 1296 16c Challis BC. Edwards A. Hunma RR. Kyrtopoulos SA. Outram JR. IARC Sci. Publ. 1978, 127 16d Challis BC. Kyrtopoulos SA. J. Chem. Soc. Perkin Trans. 1 1979, 299 17a Goldstein S. Czapski G. J. Am. Chem. Soc. 1996, 118: 3419 17b Itoh T. Matsuya Y. Maeta H. Miyazaki M. Nagata K. Ohsawa A. Chem. Pharm. Bull. 1999, 47: 819 18 Castedo L. Riguera R. Va’zquez MP. J. Chem. Soc., Chem. Commun. 1983, 301 19 Nakajima M. Warner JC. Anselme J.-P. Tetrahedron Lett. 1984, 25: 2619 20 Nudelman NS. Bonatti AE. Synlett 2000, 1825 21a Glatzhofer DT. Roy RR. Cossey KN. Org. Lett. 2002, 4: 2349 21b Nikolaides N. Ganem B. J. Org. Chem. 1989, 54: 5996 21c Garcia J. Gonza’lez J. Segura R. Urpi’ F. Vilarrasa J. J. Org. Chem. 1984, 49: 3322 21d Berenguer R. Garcia J. Vilarrasa J. Synthesis 1989, 305 22a White EH. J. Am. Chem. Soc. 1955, 77: 6008 22b Castro A. Iglesias E. Ramon Leis J. Pena ME. Va’zquez TatoJ. J. Chem. Soc. Perkin Trans. 2 1986, 1725 22c Itoh T. Nagata K. Matsuya Y. Miyazaki M. Ohsawa A. Tetrahedron Lett. 1997, 38: 5017 22d Gnewuch CT. Sosnovsky G. Chem. Rev. 1997, 97: 829 23 Zolfigol MA. Ghorbani CA. Hazarkhani H. Synlett 2002, 1002 24a Zolfigol MA. Shirini F. Ghorbani CA. Taqian-Nasab A. Keypour H. Salehzadeh S. J. Chem. Res., Synop. 2000, 420 24b Zolfigol MA. Shirini F. Ghorbani CA. Synth. Commun. 2002, 32: 1809 25a Zolfigol MA. Synth. Commun. 1999, 29: 905 25b Zolfigol MA. Shirini F. Ghorbani CA. Keypour H. Salehzadeh S. Synth. Commun. 2001, 31: 359 26a Zolfigol MA. Bamoniri A. Synlett 2002, 1621 26b Zolfigol MA. Habibi D. Mirjalili BF. Bamoniri A. Tetrahedron Lett. 2003, 44: 3345 27a Garcia J. Gonza’lez J. Segura R. Vilarrasa J. Tetrahedron 1984, 40: 3121 27b Challis BC. Milligan JR. Mitchell RC. J. Chem. Soc., Perkin Trans. 1 1990, 3103 27c Paik S. White EH. Tetrahedron Lett. 1994, 35: 7731 28 Evans DA. Carter PH. Dinsmore CJ. Barrow JC. Katz JL. Kung DW. Tetrahedron Lett. 1997, 38: 4535 29a Iranpoor N. Firouzabadi H. Zolfigol MA. Synth. Commun. 1998, 28: 2773 29b Iranpoor N. Firouzabadi H. Zolfigol MA. Synth.Commun. 1998, 28: 367 29c Iranpoor N. Firouzabadi H. Zolfigol MA. Synth. Commun. 1997, 27: 3301 29d Iranpoor N. Firouzabadi H. Heydari R. Synth. Commun. 1999, 29: 3295 29e Iranpoor N. Firouzabadi H. Heydari R. J. Chem. Res., Synop. 1999, 668 29f Iranpoor N. Firouzabadi H. Heydari R. Phosphorus, Sulfur Silicon 2002, 177: 631 29g Iranpoor N. Firouzabadi H. Pourali A.-R. Tetrahedron 2002, 58: 5179 30a Rubin B. Sisler HH. Shechter H. J. Am. Chem. Soc. 1952, 74: 877 30b Nielsen AT. Chafin AP. Christian SL. Moore DW. Nadler MP. Nissan RA. Vanderah DJ. Tetrahedron 1998, 54: 11793 31a Boyer JH. Pillai TP. Ramakrishnan VT. Synthesis 1985, 677 31b Boyer JH. Pillai TP. J. Chem. Soc., Perkin Trans. 1 1985, 1661 31c Boyer JH. Kumar G. Pillai TP. J. Chem. Soc., Perkin Trans. 1 1986, 1751 32 Gowenlock BG. Hutchison RJ. Little J. Pfab J. J. Chem. Soc., Perkin Trans. 2 1979, 1110 33 CRC Handbook of Chemistry and Physics 80 th Ed.: Lide DR. CRC Press; Boca Raton: 1999. 34 Ohwada T. Miura M. Tanaka H. Sakamoto S. Yamaguchi K. Ikeda H. Inagaki S. J. Am. Chem. Soc. 2001, 123: 10164 35 Olszewska T. Milewska MJ. Gdaniec M. Maluszynska H. Polonski T. J. Org. Chem. 2001, 66: 501 36 Anderson CC. Rodriguez F. Thurston DA. J. Appl. Poly. Sci. 1979, 23: 2453
