Oxidation of Chiral 2(5H)-Furanone Bis-Thioethers to Disulfoxides

IF 0.4 Q4 MULTIDISCIPLINARY SCIENCES
A. Khabibrakhmanova, E. S. Rabbanieva, D. Gerasimova, O. Lodochnikova, L. Latypova, A. Kurbangalieva
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引用次数: 0

Abstract

Novel disulfinyl derivatives based on 3,4-dichloro-2(5H)-furanone, aliphatic dithiols, and monoterpene alcohols were synthesized. Chiral bis-thioethers in the molecules of which the dithiol fragment links two five-membered cycles at C4 atoms were obtained in the reactions of 5(S)-(l-menthyloxy)- and 5(S)-(l-bornyloxy)-2(5H)-furanones with ethane-1,2-dithiol and propane-1,3-dithiol in acetone in basic medium. The action of an excess of m-chloroperoxybenzoic acid (2.0–3.2 equiv.) on bis-thioethers led to the formation of the corresponding mono- and disulfoxides bearing l-menthol or l-borneol fragments at the 5th position of the lactone ring. The methods of column chromatography and fractional recrystallization were used for the isolation of individual products. The structure of the synthesized heterocycles was proved by IR and NMR spectroscopy, and their composition was confirmed by high-resolution mass spectrometry. The molecular structure of the three disulfoxides was characterized by X-ray diffraction analysis.
手性2(5H)-呋喃酮双硫醚氧化制二亚砜
合成了以3,4-二氯-2(5H)-呋喃酮、脂肪二硫醇和单萜醇为基础的新型二亚砜基衍生物。在碱性介质中,5(S)-(l-甲氧基)-和5(S)-(l-甲氧基)-2(5H)-呋喃酮与乙烷-1,2-二硫醇和丙烷-1,3-二硫醇在丙酮中反应得到了手性双硫醚,其中二硫醇片段在C4原子上连接两个五元环。过量的间氯过氧苯甲酸(2.0-3.2当量)对双硫醚的作用导致在内酯环第5位形成相应的含有l-薄荷醇或l-冰片片段的单亚砜和二亚砜。采用柱层析法和分级重结晶法分离单个产物。合成的杂环化合物的结构经红外光谱和核磁共振光谱证实,组成经高分辨率质谱确证。用x射线衍射分析表征了三种二亚砜的分子结构。
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来源期刊
CiteScore
0.70
自引率
0.00%
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0
审稿时长
17 weeks
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