European Journal of Chemistry

Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines



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Zineb Hacini
Lakhdar Sekhri

Abstract

New compounds of phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines (4a-c) have been synthesized in high yields via adding n-butyl lithium in hexane to a stirred solution of methyldiphenylphosphine oxide in dry THF at 0 °C, then cooled to around -78 °C, treated with azo-pyridines(2a-c) and then allowed to warm at room temperature over 2 h. The isomers of (E)-((5-chloro-3,6-difuoro-4-(mesityldiazenyl)pyridin-2-yl)methyl)diphenyl phosphine oxide (4b) and (E)-((3,6-difuoro-4-(mesityldiazenyl)5-methoxypyridin-2-yl)methyl)diphenyl phosphine oxide (4c) can be separated on analytical HPLC: Chiralcel OD-H column, hexane:2-PrOH, (9:1, v:v) mobile phase, flow-rate, 1.0 mL/min, 25 °C, λ = 254 nm and polarimetric detection, 20 µL injection volume. The resolution of this isomers were 2.12, 1.84, respectively.


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Hacini, Z.; Sekhri, L. Synthesis and HPLC Resolution of Isomers of Novel Phosphorus Fluorinated 2,4,6-Trimethylphenylazo Pyridines. Eur. J. Chem. 2016, 7, 225-229.

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References

[1]. Palacios, F.; Alonso, C.; Santos, J. M. Chem. Rev. 2005, 105(3), 899-932.
http://dx.doi.org/10.1021/cr040672y

[2]. Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63(1-2), 193-215.
http://dx.doi.org/10.1080/10426509108029443

[3]. Hoagland, R. E. Biologically Active Natural Product; Culter, H. G., Ed.; ACS, Symposium Series 380. American Chemical Society; Washington DC, 1988, pp. 182.

[4]. Kafarski, P.; Lejezak, B. Curr. Med. Chem. Anti-Cancer Agents 2001, 1(3), 301-312.
http://dx.doi.org/10.2174/1568011013354543

[5]. Kukhar, V. P.; Hudson, H. R. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, Wiley, Chichester, 2000.

[6]. Smith, A. B.; Yager, K. M.; Taylar, C. M. J. Am. Chem. Soc. 1995, 117(44), 10879-10888.
http://dx.doi.org/10.1021/ja00149a011

[7]. Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68(6), 2410-2419.
http://dx.doi.org/10.1021/jo020707z

[8]. Palacios, F.; Aparicio, D.; Retana, A. M. O.; Santos, J. M.; Gil, J. I.; Munain, R. L. Tetrahedron Asymm. 2003, 14(6), 689-700.
http://dx.doi.org/10.1016/S0957-4166(03)00089-2

[9]. Smithrud, D. B.; Benkovic, P. A.; Benkovic, S. J.; Taylor, C. M.; Yager, K. M.; Witherington, J.; Philips, B. W.; Sprengeler, P. A.; Smith, A. B.; Hirschmann, R. J. Am. Chem. Soc. 1997, 119(2), 278-282.
http://dx.doi.org/10.1021/ja963167u

[10]. Georgiadis, D.; Dive, V.; Yiotakis, A. J. Org. Chem. 2001, 66(20), 6604-6610.
http://dx.doi.org/10.1021/jo0156363

[11]. Sekhri, L. Asian J. Chem. 2005, 17(3), 1747-1766.

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