Syntheses and Antimicrobial Activity of 2-Substituted-2,3-Dihydro-3-(4′-Bromophenyl)-1H-Naphth[1,2-e][1,3,2]Oxazaphosphorin 2-Oxides/Sulfides

The syntheses of the first examples of 2-aryloxy-2,3-dihydro-3-(4′-bromophenyl)-1H-naphth [1,2-e][1,3,2]-oxazahosphorin 2-oxides (3a-g) have been achieved from the reaction of equimolar quantities of l-(4-bromoonilinomethyl)-2-naphthol (1) with various arylphosphomdichloridates in dry toluene in the presence of triethylamine at 50-55 °C. 2-Benzyloxyl/aryloxy/arylthio/bis(2-chloroethyl)amino-2,3-dihydro-3-(4′-bromophenyl)- 1 H-naphth[1,2-e][1,3,2]-oxazaphosphorin 2-sulphides(3h-o)have been synthesized through an intermediate monochloride, namely 2chloro-2,3-dihydro-3-(4′-bromophenyl)-1H-naphth[1,3,2] oxazaphosphorin 2-sulfide (2). The structures of all products were confirmed by IR, 1 H, C and 31 P NMR data as well as via mass, spectral analysis. All compounds were screened for antibacterial activity against Bacillus subtilis and Klebsiella pneumoniae and for antifungal activity against Aspergillus niger and Curvularia lunata. A majority of the products exhibited significant activity in the assays.