40654-56-6Relevant articles and documents
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.
