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Thionation of Some α,β-Unsaturated Steroidal Ketones
Center for Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 12-16, P. O. Box. 473, 11001 Belgrade, Serbia
Faculty of Chemistry, University of Belgrade, Student ski trg 12-16, P. O. Box 158, 11001 Belgrade, Serbia
* Author to whom correspondence should be addressed.
Received: 16 April 2010; in revised form: 30 April 2010 / Accepted: 10 May 2010 / Published: 12 May 2010
Abstract: The reactions of selected α,β-unsaturated steroidal ketones with Lawesson’s reagent (LR) in CH2Cl2 and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P4S10/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, α,β-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, 1H- and 13C-NMR spectroscopy and elemental analysis.
Keywords: α,β-unsaturated steroidal ketones; α,β-unsaturated 3-thiones; Lawesson’s reagent; P4S10/HMDO; dimerization; microwave irradiation
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Krstić, N.M.; Bjelaković, M.S.; Dabović, M.M.; Pavlović, V.D. Thionation of Some α,β-Unsaturated Steroidal Ketones. Molecules 2010, 15, 3462-3477.
Krstić NM, Bjelaković MS, Dabović MM, Pavlović VD. Thionation of Some α,β-Unsaturated Steroidal Ketones. Molecules. 2010; 15(5):3462-3477.
Krstić, Natalija M.; Bjelaković, Mira S.; Dabović, Milan M.; Pavlović, Vladimir D. 2010. "Thionation of Some α,β-Unsaturated Steroidal Ketones." Molecules 15, no. 5: 3462-3477.