【作者】 刘海；

【导师】 史达清；

【作者基本信息】 苏州大学 ， 有机化学， 2010， 硕士

【摘要】 含有吲哚结构的螺环骨架广泛存在于各种天然产物中,它具有显著的生理和生物活性。甲亚胺叶立德参与的1,3-偶极环加成反应已经成为构建五元杂环重要而有效的方法。本论文研究了利用甲亚胺叶立德参与的多组分1,3-偶极环加成反应来制备含有杂环结构的螺环化合物,以及探讨了传统加热和超声波辐射对该反应的影响。本论文的研究工作分为以下四个部分:第一部分研究了利用多组分一锅法高区域和立体选择性地合成一系列新型双螺环化合物。首先,通过两分子靛红和肌氨酸及丙二腈的假四组分反应一步合成了含有两个相同吲哚片段的双螺环化合物。其次,先将靛红和丙二腈缩合制备得亲偶极体后与另一分子靛红及肌氨酸进行三组分反应可以合成含有两个不同吲哚片段的双螺环化合物。第二部分利用含有吡喃酮结构的查尔酮作为亲偶极体,与靛红衍生物、肌氨酸/硫代脯氨酸三组分在传统加热条件下进行反应,制备具有吡喃酮结构的新型螺环化合物,反应具有很高区域选择性。第三部分研究了超声波促进下甲亚胺叶立德参与的1,3-偶极环加成反应。利用超声波促进下靛红、肌氨酸和含有噻唑结构的查尔酮的三组分反应合成了一系列吡咯烷类螺环化合物。与传统的热反应相比,该方法具有反应时间缩短、产率高、后处理简单等优点。第四部分研究了超声波促进下靛红或苊醌、硫代脯氨酸和含有噻唑结构查尔酮的三组分反应,合成了一系列新型噻唑烷类双螺环化合物,反应具有很高区域选择性。更多还原

【Abstract】 The spiro compounds containing indole moiety which have significant physiological and biological activity are widely existed a variety of natural products. The 1,3-dipolar cycloaddition reaction of azomethine ylides has became an important and effective route to construction of five-membered heterocyclic ring system. In this thesis, we describe our research in detail on the preparation of spiro heterocyclic compounds by multi-component 1,3-dipolar cycloaddition reaction, and explore the reaction effect under the traditional heating and ultrasonic radiation. Four parts are included in this paper:Part one: In this part a series of novel dispiro compounds has been synthesized in high regio-selectivity and stereo-selectivity by one-pot multi-component reaction. Firstly, the pseudo-four-component reaction was investigated to synthesis of dispiro products containing two moieties of indole by the insatin, sarcosine and malononitrile with the ratio of 2:1:1 with one step. Secondly, the three components of isatin, sarcosine and dipolarophiles condensed by isatin and malononitrile were involved in forming dispiro compounds including two of different indole moieties.Part two: In this part we have studied the reaction that was taken placed under the conventional heating by three components, and the corresponding novel spiro compounds with pyrone moiety were produced in high regio-selectivity. In this reaction, the chalcones with pyrone moiety were taken as dipolarophiles, isatin derivatives and sarcosine/thioproline were treated as the source of azomethine ylides,Part three: Azomethine ylides involved in cycloaddition reactions promoted by ultrasonic radiation was studied in this part. A series of spiro compounds of pyrrole derivatives were synthesized by three components of isatin, sarcosine and chalcones with thiazole moiety under ultrasound radiation. Comparing to the traditional heating method, ultrasound chemistry takes the advantege of time saved, high yield and simple procedure.Part four: A series of novel dispiro compounds of thiazole derivatives were synthesized in high regio-selectivity by three components of isatin/ acenaphthoquinone, thioproline and chalcones with thiazole moiety under ultrasound radiation.更多还原