苯甲酰胺和硫脲衍生物的光化学性质的研究
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摘要
设计合理的光反应的条件进而合成具有特定结构和功能的光反应产物是当前光化学领域的研究热点之一。本文设计并合成了一系列苯甲酰胺和硫脲衍生物,通过选择合理的光反应条件,合成了一系列二苯甲酮和喹唑啉类化合物,应用核磁、质谱以及X-射线衍射技术对这些化合物的结构进行表征。提出了苯甲酰胺和硫脲衍生物的光反应机理。论文的主要内容如下:
1、简要介绍本论文工作的研究背景,并对苯甲酰胺和具有硫脲官能团类化合物的光化学研究进展进行简要的总结。
2、合成与表征了14个具有不同取代基的苯甲酰胺类化合物,利用紫外光谱和气相色谱确定了此类化合物较佳光照时间,测定了一个具有代表性光解产物的单晶结构,提出了苯甲酰胺类化合物的光反应机理。
3、合成与表征了7个带有不同取代基的氯代苯甲酰亚胺中间体及61个硫脲衍生物,测定了两个具有代表性化合物的单晶结构。通过实验对比我们找到了较佳的反应物的投料比、反应温度和反应所用的溶剂。
4、根据不同条件下的光反应结果,确定了硫脲衍生物的相对较好的光反应条件和光照时间,首次利用光化学手段成功得到50个具有生物活性的喹唑啉衍生物和4个具有脲基官能团的光氧化的产物,测定了两个具有代表性的喹唑啉和光氧化的产物的晶体结构。根据所得到的产物对具有硫脲基团的硫羰基化合物的光反应机理进行合理的推测。
5、合成与表征了1个环硫酮中间体和4个杂环硫酮类化合物,摸索出合成杂环硫酮中间体较佳反应条件。研究了杂环硫酮类化合物光反应,利用所得到的光产物,提出了合理的反应机理。
Design of photochemical reaction conditions and preparation of photoreaction products with special structures and functions are one of the main focuses in current fields of photochemistry. In this thesis, a series of benzamides and thioureas derivatives have been designed and prepared. By reasonable photoreaction conditions, a series of benzophenone and quinazoline compounds have been synthesized and structurally determined by NMR, MS and X-ray crystallography, respectively. The mechanisms of photoreaction of benzamide and thiureas have been proposed.This thesis includes five parts as follows.
1. The backgrounds and some relative concepts of this work are briefly introduced. The photochemistry of benzamides and compounds with thiourea functional group is also concisely reviewed.
2. Total of fourteen benzamides with different substituted groups have been synthesized and structurally characterized. Better photoreaction time for that kind of compounds at given concentrations is confirmed by tracking its’UV spectrum and GC chromatogram. A representative dibenzophenone photoproduct has been determined by X-ray crystallography. The mechanisms of photoreaction of benzamide have been proposed.
3. Total of seven N-(chloro(phenyl)methylene)benzenamines with different substituted groups and sixty-one thiourea derivatives have been synthesized and structurally characterized. Two representative compounds have been determined by X-ray crystallography. The best ratio of reactants, the adequate reaction temperature and solvent have been found by contrast experiments.
4. The better photoreaction conditions and irridation times have been confirmed through the different photoreaction results. It is the first time that fifty quinazoline derivatives with biological activity and four photooxidation products with urea functional groups have been obtained by photochemistry method. Two representative compounds, quinazoline derivatives and photooxidation products, have been determined by X-ray crystallography, respectively. The mechanism of thiocarbonyl compounds with thiourea function group has been proposed according to the photoreaction products.
5. Total of one heterocyclothione intermidate and four heterocyclothione compounds have been synthesized and structurally characterized. The photochemical reaction of heterocyclothione compounds has been investigated, and the mechanism of heterocyclothione compounds has been presumed according to the photoreaction products.
1、简要介绍本论文工作的研究背景,并对苯甲酰胺和具有硫脲官能团类化合物的光化学研究进展进行简要的总结。
2、合成与表征了14个具有不同取代基的苯甲酰胺类化合物,利用紫外光谱和气相色谱确定了此类化合物较佳光照时间,测定了一个具有代表性光解产物的单晶结构,提出了苯甲酰胺类化合物的光反应机理。
3、合成与表征了7个带有不同取代基的氯代苯甲酰亚胺中间体及61个硫脲衍生物,测定了两个具有代表性化合物的单晶结构。通过实验对比我们找到了较佳的反应物的投料比、反应温度和反应所用的溶剂。
4、根据不同条件下的光反应结果,确定了硫脲衍生物的相对较好的光反应条件和光照时间,首次利用光化学手段成功得到50个具有生物活性的喹唑啉衍生物和4个具有脲基官能团的光氧化的产物,测定了两个具有代表性的喹唑啉和光氧化的产物的晶体结构。根据所得到的产物对具有硫脲基团的硫羰基化合物的光反应机理进行合理的推测。
5、合成与表征了1个环硫酮中间体和4个杂环硫酮类化合物,摸索出合成杂环硫酮中间体较佳反应条件。研究了杂环硫酮类化合物光反应,利用所得到的光产物,提出了合理的反应机理。
Design of photochemical reaction conditions and preparation of photoreaction products with special structures and functions are one of the main focuses in current fields of photochemistry. In this thesis, a series of benzamides and thioureas derivatives have been designed and prepared. By reasonable photoreaction conditions, a series of benzophenone and quinazoline compounds have been synthesized and structurally determined by NMR, MS and X-ray crystallography, respectively. The mechanisms of photoreaction of benzamide and thiureas have been proposed.This thesis includes five parts as follows.
1. The backgrounds and some relative concepts of this work are briefly introduced. The photochemistry of benzamides and compounds with thiourea functional group is also concisely reviewed.
2. Total of fourteen benzamides with different substituted groups have been synthesized and structurally characterized. Better photoreaction time for that kind of compounds at given concentrations is confirmed by tracking its’UV spectrum and GC chromatogram. A representative dibenzophenone photoproduct has been determined by X-ray crystallography. The mechanisms of photoreaction of benzamide have been proposed.
3. Total of seven N-(chloro(phenyl)methylene)benzenamines with different substituted groups and sixty-one thiourea derivatives have been synthesized and structurally characterized. Two representative compounds have been determined by X-ray crystallography. The best ratio of reactants, the adequate reaction temperature and solvent have been found by contrast experiments.
4. The better photoreaction conditions and irridation times have been confirmed through the different photoreaction results. It is the first time that fifty quinazoline derivatives with biological activity and four photooxidation products with urea functional groups have been obtained by photochemistry method. Two representative compounds, quinazoline derivatives and photooxidation products, have been determined by X-ray crystallography, respectively. The mechanism of thiocarbonyl compounds with thiourea function group has been proposed according to the photoreaction products.
5. Total of one heterocyclothione intermidate and four heterocyclothione compounds have been synthesized and structurally characterized. The photochemical reaction of heterocyclothione compounds has been investigated, and the mechanism of heterocyclothione compounds has been presumed according to the photoreaction products.
引文
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