含氟α-羰基烯酮二硫代缩醛合成砌块研究
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摘要
本文对α-羰基烯酮二硫代缩醛类化合物的合成及应用以及含三氟甲基合成砌块在合成中的应用进行了详细的介绍。α-羰基烯酮二硫代缩醛是一类多官能团的有机化合物,具有多种化学反应性。近年来有关该类化合物的合成及其在有机合成中的应用研究取得了巨大的进展,成为有机合成中的一个研究热点。我们选择将三氟甲基引入α-羰基烯酮二硫代缩醛类化合物结构中,合成含氟α-羰基烯酮二硫代缩醛合成砌块并研究其在含三氟甲基杂环化合物合成中的应用具有重要的意义。本论文主要包括以下几方面的研究内容:
1.含氟α-羰基烯酮二硫代缩醛合成砌块的制备与结构表征。分别以三氟乙酰乙酸乙酯和三氟丙酮为原料,在碱性条件下与二硫化碳和卤代烷进行一锅法反应,制备含氟α-羰基烯酮二硫代缩醛合成砌块。其中以三氟乙酰乙酸乙酯为原料时,反应不能顺利进行。以三氟丙酮为原料,则顺利得到了4个新的含氟α-羰基烯酮二硫代缩醛化合物,最高产率为66%。利用~1H NMR、~(13)C NMR、~(19)F NMR、MS、IR和单晶X—射线衍射对化合物的结构进行了表征,化合物1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮的单晶结构测试结果表明,该化合物以二聚体的形式存在,分子晶胞以层状堆积。提出了由三氟丙酮制备含氟α-羰基烯酮二硫代缩醛合成砌块可能的反应机理。
2.含氟吡唑类化合物的合成与结构表征。利用所合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为合成砌块,分别在碱性、酸性和中性条件下与苯肼反应,探索其与肼类反应的最佳反应条件。结果表明在酸性条件下反应的产率最高。由该中间体化合物与不同取代的肼类在酸性条件下反应,得到了12个新的含氟吡唑类化合物,反应的产率为50%～82%。利用~1H NMR、~(13)C NMR、~(19)F NMR、~1H-~1H COSY、MS、IR和元素分析对化合物的结构进行了表征,提出了该反应可能的反应机理。
3.含氟苯并二氮杂卓类化合物的合成与结构表征。利用1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮合成砌块与邻苯二胺类化合物反应,得到了1个新的含氟苯并二氮杂卓类化合物。利用~1H NMR、~(13)CNMR、~(19)F NMR、MS和IR对化合物的结构进行了表征并提出了该反应可能的反应机理。
4.对本文所合成的含氟杂环化合物进行了体外抗菌性能测试。菌种为革兰氏阴性菌大肠杆菌。实验数据表明本文合成的含氟杂环化合物对大肠杆菌的抑制作用较弱。
Synthesis and application ofα-oxo ketene dithioacetals together with application of trifluoromethyl-containing building blocks to organic synthesis was reviewed.α-oxo ketene dithioacetal is a type of multi-functional organic compounds and exhibits multiple reactivity.Tremendous development has been achieved in the synthesis and application of this type of multi-functional organic compounds,which has become one of the research hotspots in the organic synthesis.Therefore,in the dissertation we choose to introduce trifluoromethyl group intoα-oxo ketene dithioacetals to prepare fuorine-containingα-oxo ketene dithioacetals as building blocks and to study their application to synthesis of trifluoromethyl-containing heterocyclic compounds.This dissertation mainly contains the following aspects:
1.Synthesis and structural characterization of fuorine-containingα-oxo ketene dithioacetals as building blocks.Ethyl trifluoroacetoacetate and trifluoroacetone were used to react with carbon disulfide and alkyl halide in one-pot reaction under a basic condition respectively to prepare fluorine-containingα-oxo ketene dithioacetals. While the reaction with ethyl trifluoroacetoacetate failed to yield the designed product, four new fluorinatedα-oxo ketene dithioacetal compounds were obtained through the one-pot reaction of trifluoroacetone with carbon disulfide and alkyl halide.The highest yield of the products reaches 66%.The structures of the new compounds were characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,MS,IR and single crystal X-ray diffraction.Results of the single crystal test on compound 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one showed that the molecules exist as dimers and accumulate in a lamellar structure.A possible reaction mechanism for the formation of fluorinatedα-oxo ketene dithioacetals from trifluoroacetone was proposed.
2.Reactions of the prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block with phenylhydrazine under acidic,basic,or neutral conditions were studied respectively to find the optimal reaction conditions.Experimental results showed that the highest yield was obtained under acidic conditions.Then the building block was used to react with a series of hydrazine compounds under acidic condition to furnish twelve new pyrazole compounds containing a trifluoromethyl group in good yields(50%～82%).The structures of the new compounds were characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,~1H-~1H COSY,MS,IR and elemental analysis.A possible mechanism for the reaction was proposed.
3.1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one was used to react with o-phenyldiamine compounds in order to synthesize fluorinated benzodiazepines.One new fluorinated benzodiazepine was obtained and its structure was characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,MS,IR.A possible mechanism for the reaction was proposed.
4.The antibaterial activity of all the synthesized trifluoromethyl-containg heterocyclic compounds was tested in vitro with the fungus Gram-negative bacteria E. coli.The data indicated that the fluorinated heterocycles showed little effect on Gram-negative bacteria E.coli.
1.含氟α-羰基烯酮二硫代缩醛合成砌块的制备与结构表征。分别以三氟乙酰乙酸乙酯和三氟丙酮为原料,在碱性条件下与二硫化碳和卤代烷进行一锅法反应,制备含氟α-羰基烯酮二硫代缩醛合成砌块。其中以三氟乙酰乙酸乙酯为原料时,反应不能顺利进行。以三氟丙酮为原料,则顺利得到了4个新的含氟α-羰基烯酮二硫代缩醛化合物,最高产率为66%。利用~1H NMR、~(13)C NMR、~(19)F NMR、MS、IR和单晶X—射线衍射对化合物的结构进行了表征,化合物1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮的单晶结构测试结果表明,该化合物以二聚体的形式存在,分子晶胞以层状堆积。提出了由三氟丙酮制备含氟α-羰基烯酮二硫代缩醛合成砌块可能的反应机理。
2.含氟吡唑类化合物的合成与结构表征。利用所合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为合成砌块,分别在碱性、酸性和中性条件下与苯肼反应,探索其与肼类反应的最佳反应条件。结果表明在酸性条件下反应的产率最高。由该中间体化合物与不同取代的肼类在酸性条件下反应,得到了12个新的含氟吡唑类化合物,反应的产率为50%～82%。利用~1H NMR、~(13)C NMR、~(19)F NMR、~1H-~1H COSY、MS、IR和元素分析对化合物的结构进行了表征,提出了该反应可能的反应机理。
3.含氟苯并二氮杂卓类化合物的合成与结构表征。利用1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮合成砌块与邻苯二胺类化合物反应,得到了1个新的含氟苯并二氮杂卓类化合物。利用~1H NMR、~(13)CNMR、~(19)F NMR、MS和IR对化合物的结构进行了表征并提出了该反应可能的反应机理。
4.对本文所合成的含氟杂环化合物进行了体外抗菌性能测试。菌种为革兰氏阴性菌大肠杆菌。实验数据表明本文合成的含氟杂环化合物对大肠杆菌的抑制作用较弱。
Synthesis and application ofα-oxo ketene dithioacetals together with application of trifluoromethyl-containing building blocks to organic synthesis was reviewed.α-oxo ketene dithioacetal is a type of multi-functional organic compounds and exhibits multiple reactivity.Tremendous development has been achieved in the synthesis and application of this type of multi-functional organic compounds,which has become one of the research hotspots in the organic synthesis.Therefore,in the dissertation we choose to introduce trifluoromethyl group intoα-oxo ketene dithioacetals to prepare fuorine-containingα-oxo ketene dithioacetals as building blocks and to study their application to synthesis of trifluoromethyl-containing heterocyclic compounds.This dissertation mainly contains the following aspects:
1.Synthesis and structural characterization of fuorine-containingα-oxo ketene dithioacetals as building blocks.Ethyl trifluoroacetoacetate and trifluoroacetone were used to react with carbon disulfide and alkyl halide in one-pot reaction under a basic condition respectively to prepare fluorine-containingα-oxo ketene dithioacetals. While the reaction with ethyl trifluoroacetoacetate failed to yield the designed product, four new fluorinatedα-oxo ketene dithioacetal compounds were obtained through the one-pot reaction of trifluoroacetone with carbon disulfide and alkyl halide.The highest yield of the products reaches 66%.The structures of the new compounds were characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,MS,IR and single crystal X-ray diffraction.Results of the single crystal test on compound 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one showed that the molecules exist as dimers and accumulate in a lamellar structure.A possible reaction mechanism for the formation of fluorinatedα-oxo ketene dithioacetals from trifluoroacetone was proposed.
2.Reactions of the prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block with phenylhydrazine under acidic,basic,or neutral conditions were studied respectively to find the optimal reaction conditions.Experimental results showed that the highest yield was obtained under acidic conditions.Then the building block was used to react with a series of hydrazine compounds under acidic condition to furnish twelve new pyrazole compounds containing a trifluoromethyl group in good yields(50%～82%).The structures of the new compounds were characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,~1H-~1H COSY,MS,IR and elemental analysis.A possible mechanism for the reaction was proposed.
3.1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one was used to react with o-phenyldiamine compounds in order to synthesize fluorinated benzodiazepines.One new fluorinated benzodiazepine was obtained and its structure was characterized with ~1H NMR,~(13)C NMR,~(19)F NMR,MS,IR.A possible mechanism for the reaction was proposed.
4.The antibaterial activity of all the synthesized trifluoromethyl-containg heterocyclic compounds was tested in vitro with the fungus Gram-negative bacteria E. coli.The data indicated that the fluorinated heterocycles showed little effect on Gram-negative bacteria E.coli.
引文
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