K. Ananda Kumar

SYNTHESIS OF SOME AMINO ACID ESTER LINKED DIOXATHIAPHOSPHOCIN/DIOXAPHOSPHOCIN DERIVATIVES

Novel 6/8-amido(methoxyglycinyl/alaninyl)dioxathiaphosphocins/dioxaphosphocins (4, 7, 10) have been synthesized from reactions of monochlorides (3,6,9) with glycine methyl ester or alanine methyl ester hydrochlorides (1a,b) at room temperature in dry tetrahydrofuran in the presence of triethylamine.

SYNTHESIS, SPECTRAL, X-RAY DIFFRACTION ANALYSIS AND ANTIMICROBIAL ACTIVITY OF 6-ARYLOXY/TRICHLOROMETHYL/CHLOROETHOXY-12-OXO-DIBENZO[d,g] [1,3,2] DIOXAPHOSPHOCIN 6-OXIDES

Abstract Syntheses of several 6-aryloxy-12-oxo-dibenzo[d,g][1,3,2] dioxaphosphocin 6-oxides (3a-i), trichloromethyl-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide (3j) and 7-chloroethoxy-12-oxo-dibenzo[d,g](1,3,2]dioxaphosphocin 6-oxide (3k) were accomplished by the reaction of equimolar quantities of 2,2′-dihydroxy benzophenone (1) with various aryl/alkyl phosphorodichloridates (2a-i,2k) and trichloromethyl phosphonicdichloride (2j) in the presence of triethylamine at 45–50[ddot]C. An X-ray diffraction analysis of 6-(4′-methyl phenoxy)-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide(3d) revealed that the dioxaphosphocin ring is in distorted-boat conformation with the “oxo” group in a pseudo equatorial arrangement and phosphoryl oxygen (P=O) in equatorial orientation in the solid state. The proposed structures of the title compounds are supported by IR, 1H, 13C and 31P NMR and Mass spectral data. Compounds 3f, 3g, 3h, 3i, 3j and 3k are found to possess significant antibacterial and antifungal activity.

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.

Solvent-free synthesis of novel 2,10-dichoro-12-trichloromethyl-6-substituted xanthato-12H-dibenzo[d,g] [1,3,2] dioxaphosphocin-6-sulfides

Abstract 2,10-Dichloro-12-trichloromethyl-6-substituted xanthato-12H-dibenzo[d,g] [1,3,2] dioxaphosphocin-6-sulfides (2a–l) with the eight-membered phosphorus and oxygen heterocyclic ring were synthesized by reacting equimolar quantities of alcohols, carbon disulfide, and 2,6,10-trichloromethyl-12H-dibenzo[d,g][1,3,2] dioxaphosphocin-6-sulfide 1 in the presence of dimethylaminopyridine (DMAP). The structures of the products were confirmed by IR, 1H, 13C, 31P-NMR, and mass spectral analyses.