三氟甲基取代氮杂环化合物的合成
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摘要
含氟杂环化合物在工业、农业以及医药上具有广泛的应用,本论文的主要目的是研究含氟α-羰基烯酮二硫代缩醛合成砌块在含三氟甲基杂环化合物合成中的应用。我们选择三氟甲基取代的氮杂环化合物为主要研究对象,以1,1,1-三氟丙酮为起始原料,合成了含氟α-羰基烯酮二硫代缩醛合成砌块；利用所合成的砌块进一步与肼、胍或邻二胺等反应,得到三氟甲基取代的氮杂环化合物。利用1H NMR、13C NMR、19F NMR、MS以及IR对新化合物的结构进行了表征,并提出了可能的反应机理。本论文主要包含以下几个方面的研究内容：
1.含氟α-羰基烯酮二硫代缩醛砌块的合成与结构表征。以1,1,1-三氟丙酮为原料,在碱性条件下与二硫化碳和卤代烃反应,得到1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮和1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮2个含氟α-羰基烯酮二硫代缩醛化合物。
2.含三氟甲基吡唑及其衍生物的合成与结构表征。以合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块与肼类物质在酸性条件下反应,得到3个三氟甲基取代的吡唑类化合物。随后,在氧化锌催化下与酰氯化合物反应,得到6个衍生物。
3.含三氟甲基二氮杂(?)的合成与结构表征。利用合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块,分别在加热和微波条件下与3,4-二氨基甲苯反应,得到2-三氟甲基-4-(3'-巯基丙硫基)-1,5-苯并二氮杂(?)化合物。
4.含三氟甲基嘧啶的合成与结构表征。以合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块,在不同醇钠和醇做溶剂的条件下与盐酸胍反应,得到3个三氟甲基取代的嘧啶类化合物。
5.含三氟甲基吡啶的合成与结构表征。以合成的1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮为砌块,与丁基锂、乙腈在低温下反应,得到三氟甲基取代的吡啶化合物中间体3-羟基-3-三氟甲基-5-硫代二苄基缩醛-4-丁烯腈。
Fluorine-containing compounds are widely used in industry, agriculture and medicine. This thesis is mainly focused on preparation ofα-oxo ketene dithioacetals and their applications to synthesis of trifluoromethyl-substituted heterocyclic compounds. Fluorine-containingα-oxo ketene dithioacetals were prepared from trifluoroacetone and were used to react with hydrazine, guanidine and o-phenylenediamine compounds to synthesis tirfluoromethyl-containing aza-heterocycles. The structures of the new compounds were characterized by 1H NMR, 13C NMR, 1 F NMR, MS and IR spectra. Possible mechanisms of the reactions were proposed. This dissertation mainly contains the following aspects:
1. Synthesis and structural characterization of fluorine-containingα-oxo ketene dithioacetals as building blocks.1,1,1-Trifluoroacetone was used to react with carbon disulfide and alkyl halide under a basic condition. Two fluorine-containingα-oxo ketene dithioacetal compounds, namely, 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one and 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one, were obtained.
2. Synthesis and structural characterization of trifluoromethyl-containing pyrazoles and their derivatives. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with hydrazines under acidic conditions and three trifluoromethyl-substitued pyrazole compounds were obtained. Then, they were used to react with acyl chlorides in the presence of zinc oxide as catalyst to afford six new derivatives.
3. Synthesis and structural characterization of trifluoromethyl-containing diazepines. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with o-phenylenediamine compounds under heating and microwave conditions, respectively to obtain a diazepine compound 2-trifluoromethyl-4-(3'-mercaptopropylthio)-1,5-benzosdiazepine.
4. Synthesis and structural characterization of trifluoromethyl-containing pyrimidines. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with guanidine in various solvents to obtain three trifluoromethyl-substitued pyrimidine compounds.
5. Synthesis and structural characterization of trifluoromethyl-containing pyridines. The prepared 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one as a building block was used to react with n-butyl lithium and acetonitrile at low temperature and an intermediate of trifluoromethyl-substituted pyridine, namely,3-hydroxy-3-trifluoromethyl-5-thiodibenzyl-acetal-4-butenenitrile, was obtained.
1.含氟α-羰基烯酮二硫代缩醛砌块的合成与结构表征。以1,1,1-三氟丙酮为原料,在碱性条件下与二硫化碳和卤代烃反应,得到1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮和1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮2个含氟α-羰基烯酮二硫代缩醛化合物。
2.含三氟甲基吡唑及其衍生物的合成与结构表征。以合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块与肼类物质在酸性条件下反应,得到3个三氟甲基取代的吡唑类化合物。随后,在氧化锌催化下与酰氯化合物反应,得到6个衍生物。
3.含三氟甲基二氮杂(?)的合成与结构表征。利用合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块,分别在加热和微波条件下与3,4-二氨基甲苯反应,得到2-三氟甲基-4-(3'-巯基丙硫基)-1,5-苯并二氮杂(?)化合物。
4.含三氟甲基嘧啶的合成与结构表征。以合成的1,1,1-三氟-4-硫代缩丙醛-3-丁烯-2-酮为砌块,在不同醇钠和醇做溶剂的条件下与盐酸胍反应,得到3个三氟甲基取代的嘧啶类化合物。
5.含三氟甲基吡啶的合成与结构表征。以合成的1,1,1-三氟-4-硫代二苄基缩醛-3-丁烯-2-酮为砌块,与丁基锂、乙腈在低温下反应,得到三氟甲基取代的吡啶化合物中间体3-羟基-3-三氟甲基-5-硫代二苄基缩醛-4-丁烯腈。
Fluorine-containing compounds are widely used in industry, agriculture and medicine. This thesis is mainly focused on preparation ofα-oxo ketene dithioacetals and their applications to synthesis of trifluoromethyl-substituted heterocyclic compounds. Fluorine-containingα-oxo ketene dithioacetals were prepared from trifluoroacetone and were used to react with hydrazine, guanidine and o-phenylenediamine compounds to synthesis tirfluoromethyl-containing aza-heterocycles. The structures of the new compounds were characterized by 1H NMR, 13C NMR, 1 F NMR, MS and IR spectra. Possible mechanisms of the reactions were proposed. This dissertation mainly contains the following aspects:
1. Synthesis and structural characterization of fluorine-containingα-oxo ketene dithioacetals as building blocks.1,1,1-Trifluoroacetone was used to react with carbon disulfide and alkyl halide under a basic condition. Two fluorine-containingα-oxo ketene dithioacetal compounds, namely, 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one and 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one, were obtained.
2. Synthesis and structural characterization of trifluoromethyl-containing pyrazoles and their derivatives. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with hydrazines under acidic conditions and three trifluoromethyl-substitued pyrazole compounds were obtained. Then, they were used to react with acyl chlorides in the presence of zinc oxide as catalyst to afford six new derivatives.
3. Synthesis and structural characterization of trifluoromethyl-containing diazepines. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with o-phenylenediamine compounds under heating and microwave conditions, respectively to obtain a diazepine compound 2-trifluoromethyl-4-(3'-mercaptopropylthio)-1,5-benzosdiazepine.
4. Synthesis and structural characterization of trifluoromethyl-containing pyrimidines. The prepared 1,1,1-trifluoro-4-thiopropionacetal-3-buten-2-one as a building block was used to react with guanidine in various solvents to obtain three trifluoromethyl-substitued pyrimidine compounds.
5. Synthesis and structural characterization of trifluoromethyl-containing pyridines. The prepared 1,1,1-trifluoro-4-thiodibenzylacetal-3-buten-2-one as a building block was used to react with n-butyl lithium and acetonitrile at low temperature and an intermediate of trifluoromethyl-substituted pyridine, namely,3-hydroxy-3-trifluoromethyl-5-thiodibenzyl-acetal-4-butenenitrile, was obtained.
引文
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[3]梁诚.含氟医药的合成技术与生产现状[J].有机氟工业,2003,1：21-27.
[4]Shimizu R., Egami H., Nagi T., et al. Direct C2-trifluoromethylation of indole derivatives catalyzed by copper acetate[J]. Tetrahedron Lett.,2010,51:5947-5949.
[5]Wiehn M.S., Vinogradova E.V., Ekaterina V., et al. Electrophilic trifluorom-ethylation of arenes and N-heteroarenes using hypervalent iodine reagents[J]. J. Fluorine Chem.,2010,131:951-957.
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