M. F. Stephen Babu

Syntheses of substituted 8-(aminobenzyl)dinaphthodioxaphosphocine 8-oxides

Substituted (8-aminobenzyl)dinaphthodioxaphosphocine 8-oxides were prepared in a two-step process. The first step of the reaction is one-pot synthesis of α-aminophosphonates by the reaction of aldehydes, amines, and trialkyl phosphite in the presence of ceric ammonium nitrate. The second step is cyclization of α-aminophosphonates with bis(2-hydroxy-1-naphthyl)methane in the presence of a catalytic amount of p toluenesulphonic acid under reflux conditions. Their structures were established by elemental analyses, IR, 1H, 13C, 31P NMR, and mass spectral data.

Synthesis, Spectral, and Antimicrobial Activity of 6-Alkylcarbamato-2,10-dichloro-12- trichloromethyl-12 H -dibenzo[d,g][1,3,2]- dioxaphosphocin 6-Oxides

Abstract 6-Alkylcarbamato/alkylthiocarbamato-2,10-dichloro-12-trichloromethyl-12H-dibenzo[d,g][1,3,2]-dioxaphosphocin 6-oxides (4a–f) have been synthesized by the condensation of 2,2-bis-(2-hydroxy-5-chlorophenyl)-1,1,1-trichloroethane (3) with dichlorophosphinyl carbamates (2a–f) of different alcohols/thiols in the presence of triethylamine in dry toluene. The title compounds structures were confirmed by different spectral (elemental, IR and 1H, 13C & 31P NMR) studies and found to possess antimicrobial activity.

SYNTHESIS AND SPECTRAL STUDIES OF NOVEL 2-CHLOROETHYL DIOXA/DIOXATHIAPHOSPHOCINS AND BENZODIAZAPHOSPHOLE 2/6/8-OXIDES

Abstract Anew class of phosphonates, 2,10-dichloro-l2-trichloromethyl-6-(2-chloroethy1)-12H-dibenzo [d,g] [1,3,2]dioxaphosphocin 6-oxide 3a, 2,10-dichloro-6-(2-chloroethyl) dibenzo [d,g] [1,3,6,2] dioxathiaphosphocin 6-oxide 3b, 8-(2-chloroethyl)-16H-dinaphtho[2,1-d:1,2′-g] 1,3,2-dioxaphosphocin 8-oxide 5, 2, 10-dichloro-6-(2-chloroethyl)-4,8-dinitrodibenzo[d,g] [1,3,6,2] dioxathiaphosphocin 6-oxide 9 and 2-(2-chloroethy1)2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide 13 have been synthesized from reactions of equimolar quantities of diols (2a,2b,4,7)/diamine (12) with 2-chloroethyl phosphonyl dichloride I at various temperatures in dry toluene in the presence of triethylamine. Oxidation studies with H2O2 (30%) in acetic acid showed interesting results. Compound 9 on oxidation yielded only the corresponding 12-sulphoxide (10) and not its sulphone (11). But similar oxidation of 13 afforded sulphone (14), thus showing that steric and electronic factors control the oxidation process. Alternative approach for the preparation of 11 by oxidation of 7 to sulphone 8 and its cyclocondensation with 1 were unsuccessful due to the existence of strong intramolecular H-bonding. Their IR, 1H, 13C, 31P NMR and mass spectral data were analyzed.