International Journal of Chemical and Biomolecular Science
Articles Information
International Journal of Chemical and Biomolecular Science, Vol.5, No.2, Jun. 2019, Pub. Date: Apr. 26, 2019
N-Dealkylation of Dialkylanilines: Role of Oxidizing Agents on Product Selectivity
Pages: 29-33 Views: 360 Downloads: 200
[01] Daisy Bhat, Department of Applied Sciences, R. D Foundation Group of Institutions (AKTU), Kadrabad Modinagar Ghaziabad Uttar Pradesh, India.
[02] Yamini Sarada, Department of Applied Sciences, Northern India Engineering College (IPU), Shastri Park Delhi, India.
Large varieties of pharmaceuticals metabolize involving dealkylation of their important functional groups. N Dealkylation of Tertiary amines is one of the most important biochemical processes of Cytochrome P-450, which play major role in Drug metabolism. Efficiency of pharmaceutical compounds depends on their metabolic patterns inside the body. Development of newer and better drugs requires understanding of their metabolism under different reaction conditions. Having keen interest in study of N-Dealkylation process, We are herein reporting investigation into the role of oxidising species on N-Dealkylation of dialkyl anilines, NN Dimethylaniline (NDMA) and NNdiethylaniline (NDEA) with metal complexes as catalyst Dialkylanilines gave corresponding N-dealkylated and monoxygenated compounds as products with molecular oxygen as oxidizing agent. Replacement of molecular oxygen with Tetraethyl ammoniumperiodate (TEAPI) as oxidant using same set of reactions, gave N- alkyl formanalide as major product. TEAPI shifted the selectivity of products towards the mono oxygenated product as compared to molecular oxygen. TEAPI facilitates oxygen atom transfer to the substrate and tilts the product selectivity towards N-alkyl formanalide formation
Dealkylation, Metal Complex, TEAPI, Molecular Oxygen
[01] N. Kasi, M. SookSeo, K. Jinheung, N. Wonwoo, Inorg. Chem. 2007, 46, 293−298.
[02] C. Walch. Enzymatic Reaction Mechanism, Freeman CO., San Fransisco, 1979.
[03] N. Murugesan, S. M. J. Hecht, Am. Chem. Soc. 1985; 107: 493–500.
[04] A. de. Klerk, Fischer Tropsch Refining, John Wiley 2012.
[05] J. P. Speight Environmental Organic Chemistry for Engineers, Chap. 3 Butterwork Heinmann (Elsevier) 2017.
[06] J. H. Cooley, E. J. Evain, Synthesis 1989, 1 (and the references therein). doi: 10.1055/S-1989-27129.
[07] L. Que, R. Y. N. Ho, Chem. Rev. 1996, 96, 2607. doi: 10.1021/ CR960039F.
[08] F. P. Guengerich. Chem. Res. Toxi. 2008; 21: 70–83.
[09] H. Dong, R. L. Helning, E. L. Thummel, AE, Rettle, S. D. Nelson, Drug Matabolism and Deposition 2008; 28: 1397–1400.
[10] R. E. McMohan. J. Am. Pharm. Assoc. 1947; 55: 267–271.
[11] M, Stilborova, H. H. Shmeiser E. Frei. Phytochem. 2000; 54: 353–362.
[12] R. S. Mane, B. M. Bhange, J. Org. Chem. 2016, 81 (12), 4974-4980.
[13] D. Bhat, N. Sharma, Aust. J. Chem. 2017, 70, 233–236.
[14] D. D. Agarwal, D. Bhat, J. Porphyrins Phthalocyanines 2016, 20: 689–693.
[15] A. I. Vogel, Text Book of Practical Organic Chemistry 1978.
[16] D. Bhat, Asian Chem. Lett. 2006, 10, 157.
[17] P Bhyrappa, V. Krishnan. Inorg. Chem. 1991; 30: 239.
[18] V. Krishana, D. D. Agarwal, G. Bhayrappa, R. Rastogi, Indian J. Chem., Sect. A: Inorg., Phys., Theor. Anal. 1998, 37, 918.
[19] R. P. Hanzlik, R. H. Tullman, J. Am. Chem. Soc. 1982, 104, 2048. doi: 10.1021/JA00371A055.
[20] T. L. Macdonald, K. Zirvi, L. T. Burka, P Peyman, F. P. Guengerich, J. Am. Chem. Soc. 1982, 2050. doi: 10.1021/JA00371A056.
[21] J. R. Lindsay Smith, D. N. Mortimer, J. Chem. Soc., Perkin Trans. 11986, 2, 1743. doi: 10.1039/P29860001743.
[22] F. P. Guengerich, T. L. Macdonald, Acc. Chem. Res. 1984, 17, 9. doi: 10.1021/AR00097A002.
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