MNTf23催化合成2苯基苯并噻唑类化合物.pdf

华中科技大学硕士学位论文 I摘要苯并噻唑的衍生物具有抗菌、抗癌活性,荧光性和光致变色性等性质,在生理及光学的研究与开发方面有着广泛的应用。全氟烷基磺酰亚胺的盐类作为一类新型的Lewis酸被广泛应用于催化许多有机合成反应。本文主要研究了以三氟甲基磺酰亚胺的盐(M(NTf2)3)为催化剂,催化合成2-取代苯并噻唑类化合物的方法。本论文的工作主要包括了以下方面:优化了作为合成2-取代苯并噻唑类化合物常用的原料——邻氨基苯硫酚的合成方法。在现有的合成方法的基础上,通过对合成方法的优化和改进,能够比较方便和经济的合成该化合物,并对一些新的合成方法进行了探索。研究了催化合成2-取代基苯并噻唑化合物的方法。通过三氟甲基磺酰亚胺的盐和三氟甲基磺酸盐的催化合成2-苯基苯并噻唑的对比,发现在THF中,三氟甲基磺酸盐有较好的催化效果,另一方面,在硝基甲烷中,三氟甲基磺酰亚胺盐则有更好的催化效果。通过对反应时间,反应温度,以及催化剂用量等反应条件的研究,确定了以下的优化的反应条件:在通入氧气的条件下,加入2 mol%的催化剂,在室温下反应2 h,反应的产率就能达到90%以上。在上述反应条件下,研究了三氟甲基磺酰亚胺盐催化合成2-取代基为其他取代基(呋喃基,对硝基苯基,丙基)的苯并噻唑类化合物。通过实验证明了,对于催化合成取代基为呋喃基化合物,三(三氟甲基磺酰亚胺)钐盐较之三氟甲基磺酸盐有较大的优势。本文通过一系列的实验对反应条件进行了优化,建立了一个新的有效的合成2-取代苯并噻唑的新方法。关键词:催化合成三氟甲基磺酰亚胺盐 2-取代苯并噻唑邻氨基苯硫酚华中科技大学硕士学位论文 IIAbstract Benzothiazole derivatives with antibacterial, anti-cancer activity, fluorescence and photochromic activity, are widely applied in physical and optical research and development. As a series of highly efficient catalysts, perfluoroalkyl methyl polyimide salts as novel Lewis acids are diffusedly used for anic synthesis. This paper is about method to synthesis for 2-substituted pound by trifluoromethyl methyl imide salt (M(NTf2)3). In this paper, the work includes the following two aspects: We optimized the method of prepared for o-aminothiophenol used for synthesis of 2 -substituted monly. Based on the reported synthesis methods , through the optimization and improvement of the method ,we found a new way in which it can be more convenient and economy to get a certain amount of pound. And as well a novel synthetic method has been explored. On the 2-subsitituted pounds of synthesis approach, through trifluoromethylimide and trifluoromethyl sulfonate salts 2-phenyl benzothiazole catalytic synthesis contrast, we found that in solvent THF, trifluoromethyl sulfonate salts is a good catalyst, while, in the nitromethane, trifluoromethyl imide salt has a better catalytic effect. The reaction condition, such as the reaction time, temperature and the amount of catalyst, has bee