Synthesis, spectral, X-ray diffraction analysis and antimicrobial activityof 6-aryloxy trichloromethyl chloroethoxy-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin-6-oxides

Syntheses of several 6-aryloxy-12-oxo-dibenzo[d,g][1,3,2] dioxaphosphocin 6 -oxides (3a-i), trichloromethyl-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6 -oxide (3j) and 2-chloroethoxy-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6- oxide (3k) were accomplished by the reaction of equimolar quantities of 2,2 '-dihydroxy benzopbenone (1) with various aryl / alkyl phosphorodichloridat es (2a-i,2k) and trichloromethyl phosphonicdichloride (2j) in the presence of triethylamine at 45-50 degreesC. An X-ray diffraction analysis of 6-(4'- methyl phenoxy)-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide(3d) revea led that the dioxaphosphocin ring is in distorted-boat conformation with th e "oxo" group in a pseudo equatorial arrangement and phosphoryl oxygen (P=O ) in equatorial orientation in the solid state. The proposed structures of the title compounds are supported by IR, H-1, C-13 and P-31 NMR and Mass sp ectral data. Compounds 3f, 3g, 3h, 3i, 3j and 3k are found to possess signi ficant antibacterial and antifungal activity.