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 ' -bromoph enyl)-1H-naphth [1,2-e] [1,3,2]-oxazahosphorin 2-oxides (3a-g) have been ac hieved from the reaction of equimolar quantities of 1-(4-bromoanilinomethyl )-2-naphthol (1) with various arylphosphorodichloridates in dry toluene in the presence of triethylamine at 50-55 degreesC. 2-Benzyloxy/aryloxy/arylth io/bis(2-chloroethyl)amino-2,3-dihydro-3-(4 ' -bromophenyl)-1H-naphth[1,2-e ] [1,3,2]-oxazaphosphorin 2-sulfides (3h-o) have been synthesized through a n intermediate monochloride, namely 2-chloro-2,3-dihydro-3-(4 ' -bromopheny l)-1H-naphth[1,2-e][1,3,2]oxazaphosphorin 2-sulfide (2). The structures of all products were confirmed by IR,H-1, C-13 and P-31 NMR data as well as vi a mass spectral analysis. All compounds were screened for antibacterial act ivity against Bacillus subtilis and Klebsiella pneumoniae and for antifunga l activity against Aspergillus niger and Curvularia lunata. A majority of t he products exhibited significant activity in the assays.