Novel fluorine substituted α-amino
phosphonic acids containing 1,2,4-triazin- 5-one (6a-f) have been obtained from
fluoroacylation of 6-(2′-amino-5′-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one
(1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic
aldehydes yielded the Schiff bases 4. The simple addition of diethyl
phosphonate to compound 4 produced the α-amino phosphonates 5.
Acidic hydrolysis of compound 5 produced the
fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have
been established with the help of elemental analysis and spectral measurements.
Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.
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