Synthesis and bioactivities of novel 1,3,2-dioxaphosphorinane-2-one containing arylglyoxylonitrile oxime

The reaction of trans-2-chloro-2-oxo-4-phenyl-5,5-dimethyl-1,3,2-dioxaphosp horinane( II) with arylglyoxylonitrile oximes in the presence of PTC result ed in diastereomers of novel cyclic phosphate of arylglyoxylonitrile oxime (III), The configuration and ratio of cis/trans diastereomers of III were c onfined by H-1 NMR, P-31 NMR and X-ray diffraction analysis, The reaction o f arylaldoxime with trans- II yielded an unstable arylaldoxime cyclic phosp hate which was decomposed through Beckmann fragmentation to give nitrile an d cyclic phosphate acid, The bioassay indicated that compound cis-III showe d a high antiviral activity against TMV.