Thionation of some alpha,beta-unsaturated steroidal ketones.
The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.
Krstić
Natalija M
NM
Center for Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 12-16, P. O. Box. 473, 11001 Belgrade, Serbia. nkrstic@chem.bg.ac.rs
Bjelaković
Mira S
MS
Dabović
Milan M
MM
Pavlović
Vladimir D
VD
D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents; D013256:Steroids / Q000737:chemistry*; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry*
D007202:Indicators and Reagents; D007659:Ketones; D012997:Solvents; D013256:Steroids; D013871:Thiones