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一些α,β-不饱和甾酮的硫醚化反应。

Thionation of some alpha,beta-unsaturated steroidal ketones.

机构信息

Center for Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 12-16, P. O. Box. 473, 11001 Belgrade, Serbia.

出版信息

Molecules. 2010 May 12;15(5):3462-77. doi: 10.3390/molecules15053462.

Abstract

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.

摘要

研究了在标准反应条件下,Lawesson 试剂(LR)与 CH(2)Cl(2)和甲苯中选定的α,β-不饱和甾体酮的反应,以及在微波辐射下,五硫化二磷与六甲基二硅氧烷(P(4)S(10)/HMDO)在 1,2-二氯苯(ODCB)中的组合反应,并为此选择了几种胆甾烷、雄烷和孕烷羰基衍生物。根据试剂和溶剂的不同,合成了 19 种新的含硫化合物,包括二硫代 4c 和 4d、α,β-不饱和 3-硫酮 3a-e、二聚硫醚 2a-e、1,2,4-三硫杂环戊烷 5a-e 和膦酸三硫酯 6b-e。所有新制备的化合物均通过 IR、(1)H-和(13)C-NMR 光谱以及元素分析进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8507/6257495/63095295193e/molecules-15-03462-g001.jpg

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