Synthesis and antimicrobial activity of 2,10-dichloro-6-substituted-4,8-dinitro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides/sulfides

Abstract

Novel 2,10-dichloro-6-substituted-4,8-dinitro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides (4a–h) were synthesized by reacting 5,5′-dichloro-3,3′-dinitro-2,2′-dihydroxydiphenylmethane (2) with different aryl phosphorodichloridates (3a–g) or bis(2-chloroethyl)phosphoramidic dichloride (3h) in the presence of triethylamine at 55–60°C, and the compounds 4i–l were prepared by reacting the 2,6,10-trichloro-4,8-dinitro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-sulfide (5) in situ with substituted phenols and thiophenol 5 was prepared by condensing 2 with thiophosphoryl chloride. IR, 1H, 13C, 31P NMR, and mass spectra supported all the proposed structures. Several title compounds exhibited significant activity in the assays against the bacteria Bacillus subtilis and Escherichia coli and fungi Curvularia lunata and Aspergillus niger. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:10–15, 2001