40654-56-6Relevant academic research and scientific papers
Synthesis and spectral studies (see abstract)
Rao, L. Nagaprasada,Reddy, C. Devendranath,Reddy, V. Krishna,Hagar, Jacob D.,Tran, Kevin,Berlin, K. Darrell
, p. 399 - 410 (2002)
Several novel bis(2-chloroethyl)aminophosphoryl-containing compounds have been prepared as potential anticancer agents. 2,10-Dichloro-6-[bis(2-chloroethyl)]amino-4,8-dinitrodibenzo[d,g][1,3,6,2]- dioxathiaphosphocin 6-oxide (5), 2-bis(2-chloroethyl)amino-1,3, 2-dioxaphosphorinane 2-oxide (13), and 8-bis(2-chloroethyl)amino-6H-dinaphtho[2,1-d:1prime;,2′]1,3,2- dioxaphosphocin 8-oxide (15) were synthesized from a reaction of equimolar quantities of the corresponding precursor diols 3, 12, and 14 with coreagent N,N-bis(2-chloroethyl)-phosphoramidic dichloride (1) at various temperatures in dry toluene/ether in the presence of triethylamine. In addition, 2-bis(2-chloroethyl)amino-2,3-dihydro-5-thiophenoxy-1H-1,3,2- benzodiazaphosphole 2-oxide (9) and 2-bis(2-chloroethyl)amino-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorinane 2-oxide (11) were derived from 4-thiophenoxy-1,2-diphenyldiamine (8) and 2-aminobenzylamine (10) respectively, under similar conditions. Interestingly, attempted oxidation of 5 to the corresponding sulfone 7 by H2O2 (30%) in acetic acid yielded only sulfoxide 6 [2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2] dioxathiaphosphocin 6-oxide}. In an alternative approach, oxidation of 5,5′-dichloro-3,3′-dinitro-2,2′-dihydroxydiphenyl sulfide (3) with H2O2 (30%) in acetic acid formed the corresponding sulfone 4. However, attempted cyclization of 4 with 1, in the presence of triethylamine, to give the sulfone expected from 5 was unsuccessful. NMR analysis of 6 suggests the presence of two conformers in solution.
Synthesis and spectral studies of novel 2-chloroethyl dioxa / dioxathiaphosphocins and benzodiazaphosphole 2/6/8-oxides
Naga Prasada Rao,Stephen Babu,Vasugovardhana Reddy,Devendranath Reddy,Suresh Reddy
, p. 211 - 222 (2007/10/03)
A new class of phosphorates, 2, 10-dichloro-12-trichloromethyl-6-(2-chloroethyl)-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-chloroethyl)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 1 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.
