含噻唑环吲哚-2-酮新型衍生物的合成研究

发布时间：2018-03-28 01:03

  本文选题：吲哚二酮　切入点：噻唑　出处：《湖南科技大学》2017年硕士论文

【摘要】：吲哚二酮类化合物和噻唑类化合物是受许多科研工作者青睐的杂环化合物,医用药物领域里的不少具有生物活性的药物分子中都存在着这两种结构,带有这两类基团的化合物一般都具有良好的生物活性,譬如抗真菌,抗癌,抗肿瘤,抗抑郁以及消炎等。本论文设计并合成了一系列含噻唑环吲哚-2-酮新型衍生物。运用了IR、MS、~1HNMR和13CNMR等现代光谱技术分析手段对该系列化合物的结构进行了表征。本研究的主要研究成果如下:一、采用改进方法以吲哚二酮与取代氯化苄反应生成中间产物1-取代-吲哚-2,3-二酮1,再用中间产物1-取代-吲哚-2,3-二酮1与硫代氨基脲反应生成中间产物1-取代-吲哚-2,3-二酮缩氨基硫脲2。二、利用已合成的中间产物1-取代-吲哚-2,3-二酮缩氨基硫脲2与2-溴苯乙酮在以冰乙酸为催化剂的条件下反应成环得到目标产物1-取代-3-(5-苯基噻唑-2-基)亚联氨基吲哚-2-酮3,最后对合成条件进行了优化,得到了较优的合成条件为:间产物2与2-溴苯乙酮比例为1;1.3时,C2H5OH为溶剂,体系温度为60℃,反应时间5.5h,催化剂为冰乙酸。三、利用中间产物1-取代-吲哚-2,3-二酮缩氨基硫脲2与2-氯乙酰乙酸乙酯在以冰乙酸为催化剂的条件下反应成环,得到目标产物1-取代-3-(4-甲基-5-乙氧甲酰基噻唑-2-基)亚联氨基吲哚-2-酮4,最后对合成条件进行了优化,得到了较优的合成条件。以中间产物2与2-氯乙酰乙酸乙酯比例为1;1.3时,C2H5OH为溶剂,体系温度为70℃,反应用时6.5h,催化剂为冰乙酸。
[Abstract]:Indole diketones and thiazoles are heterocyclic compounds favored by many researchers, and many bioactive drug molecules in the field of medical medicine have these two structures. Compounds with these two groups generally have good biological activities, such as antifungal, anticancer, anti-tumor, In this paper, a series of novel derivatives containing thiazolidocycloindole-2-one were designed and synthesized. The structures of these compounds were characterized by modern spectroscopic techniques such as 1H NMR and 13CNMR. The main research results are as follows: 1. The intermediate product 1- substituted indole-2o 3-dione was synthesized by the reaction of indole diketone with substituted benzyl chloride, and the intermediate product 1-substituted-2-indole-2-diketone 1 was reacted with thiosinicarbazone to form the intermediate product 1-substituted-Indole-indandione. 3-diketone thiosemicarbazone. The target product 1-substituted-3-phenylthiazolyl) was synthesized by the reaction of 1-substituted-indole-2-2-diketone thiosemicarbazone with 2-bromoacetophenone in the presence of glacial acetic acid as catalyst. Finally, the synthesis conditions were optimized. The optimum synthesis conditions were obtained as follows: when the ratio of mesophosphate 2 and 2-bromoacetophenone was 1o 1.3, C _ 2H _ 5OH was used as solvent, the system temperature was 60 鈩，

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