Synthesis and Biological activity of novel phosphorus fluorinated

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A combination of fluorinated and diphenylphosphinoyl groups in azo-compounds and thier corresponding diazepines compounds will hopefully make them very interesting biological active compunds.

It was therefore decided to investigation the synthesis of this type of the compounds.

New compound of phosphorus fluorinated 2, 4, 6- Trimethyl Phenyl azo Pyridines and their corresponding diazepines have been synthesized in high yields via adding n-buLi in hexane to a stirred solution of methyldiphenylphosphine oxide in dry THF at 0°C, then cooled to around -78°C, treated with (2,4,6 trimethylphenylazopyridines and then allowed to warm at room temperature over 2 hours.

The isomers of (E)-((5-chloro-3,6-difuoro4-(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) was 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, 20μL injection volume.

The resolution of this isomers were 2.12, 1.84, respectively.

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