Synthesis and antibacterial activity of 2-alkylcarbamato/trichloromethyl/chloroethoxy/aryloxy-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine 2-oxides

Several 2-trichloromethyl/2-chloro-ethoxy/2-aryloxy-1,2,3,4-tetrahydro-1,3,2-benzodiaza-phosphorine 2-oxides (4a–d), and 2-alkyl/alkenyl/alkynylcarbamato 2-oxides (7a-f) have been synthesized from reactions of equimolar quantities of 2-aminobenzylamine (2) with various aryl or alkyl phosphorodichloridates (3b–d), trichloromethylphosphonic dichloride (3a) and dichlorophosphinyl carbamates (6a–f) at 40–50°C in dry toluene in the presence of triethylamine. IR, ¹H, ¹³C, ³¹P NMR and mass spectral analyses were collected and analyzed and supported all structures. The title compounds were screened for antibacterial activity against Bacillus subtilis and Escherichia coli. Several of the agents exhibited significant activity in the assays. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:323–328, 2000