Bismuth chloride-sodium nitrite: A novel reagent for chemoselective N-nitrosation

Synthetic Communications

Volumn 39, Issue 4, 2009, Pages 604-612

  Chaskar, Atul C ^a   Langi, Bhushan P ^a   Deorukhkar, Amol ^b   Deokar, Hrushikesh ^a  

^a C K Thakur Research Centre   (India)

^b INSTITUTE OF SCIENCE   (India)

Author keywords

Bismuth(III) chloride; N nitrosation; Nitrosamides; Nitrosamines; Nitrosotetrazoles

Indexed keywords

AMIDE; AMINE; BISMUTH; NITROGEN; NITROSO DERIVATIVE; SODIUM NITRITE; TETRAZOLE DERIVATIVE;

ARTICLE; NITROSATION;

EID: 61849101780     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802413881     Document Type: Article

References (20)

1. Moncada, S.; Palmer, R. M.; Higgs, E. A. Nitric oxide: Physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 1991, 43, 109.
2. Kostyukovskii, Y. L.; Melamed, D. B. Carcinogenic N-nitrosamines: Formation, properties, and analysis. Russ. Chem. Rev. 1988, 57, 350.
3. Seebach, D.; Wykypiel, W. Safe one-pot carbon-carbon bond formation with lithiated nitrosamines including denitrosation by sequential reduction with lithium aluminium hydride and Raney-nickel. Synthesis 1979, 423.
4. Touster, O. Determination of keto-enol equilibrium constants and the kinetic study of the nitrosation reaction of β-dicarbonyl compounds. In Organic Reactions; Wiley: New York, 1953; vol. 7, chap 6.
5. Williams, D. L. H. Nitrosation Reactions and the Chemistry of Nitric Oxide, 1st ed.; Elsevier Science: Amsterdam, Oxford, 2004.
6. Garcia Rio, L.; Leis, J. R.; Iglesias, E. Nitrosation of amines in nonaqueous solvents, 1: Evidence of a stepwise mechanism. J. Org. Chem. 1997, 62, 4701.
7. Leis, J. R.; Peña, M. E.; Rios, A. M. Nucleophilic reactivity towards 'normal' and ambidentate electrophiles bearing the nitroso group A. J. Chem. Soc., Perkin Trans. 2 1995, 587.
8. 2 and evidence for common intermediates. J. Am. Chem. Soc. 2000, 122, 6911.
9. Castedo, L.; Riguera, R.; Vazquez, M. P. Fremy's salt (potassium nitrosodisulphonate): A nitrosating reagent for amines. J. Chem. Soc. Chem. Commun. 1983, 301.
10. Chang, S. K.; Harrington, G. W.; Rothstein, M.; Shergalis, W. A.; Swern, D.; Vohra, S. K. Accelerating effect of ascorbic acid on N-nitrosamine formation and nitrosation by oxyhyponitrite. Cancer Res. 1979, 39, 3871.
11. Cova, D.; Nebuloni, C.; Arnoldi, A.; Bassoli, A.; Trevisan, M.; Del Re, A. A. M. N-Nitrosation of triazines in human gastric juice. J. Agric. Food. Chem. 1996, 44, 2852.
12. 2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions. Tetrahedron Lett. 2003, 44, 3345.
13. -]. J. Org. Chem. 2001, 66, 3619.
14. 4). Synthesis 2003, 1591.
15. 4/charcoal): Selective nitrosation of amines, amides, ureas, and thiols. Synth. Commun. 2005, 35, 1517.
16. Fanning, J. C.; Keefer, L. K.; Larry, K. Rapid formation of a potent nitrosating agent by solvolysis of ionic nitrite in dichloromethane. J. Chem. Soc., Chem. Commun. 1987, 955.
17. Demir, A. S.;Mahasneh, A. S.;Aksoy, H.; Gercek, Z. The mild N-nitrosation of secondary amines with trichloro nitromethane. Synth. Commun. 1992, 22, 2607.
18. X gases: Encapsulated reagents for nitrosation. Chem. Eur. J. 2005, 11, 1924.
19. Zolfigol, M. A. Efficient and chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions with sodium nitrite and oxalic acid two hydrate. Synth. Commun. 1999, 29, 905.
20. 2 as a novel heterogeneous system for the N-nitrosation of N,N-dialkylamines under mild conditions. Synlett 2002, 1002.