论文部分内容阅读
噻吩和呋喃衍生物是许多天然产物、药物和发光材料的核心骨架,因此发展一种从简单易得的原料高效合成呋喃和噻吩衍生物的方法具有非常重要的应用价值.该研究实现了一锅法高产率合成2,5-二取代呋喃、2,5-二取代噻吩、苯并呋喃和苯并噻吩化合物.首先通过铜催化末端炔烃Glaser偶联反应合成1,4-二取代丁二炔化合物,接着硫化钠(氢氧化钾)参与水解和环化反应得到2,5-二取代噻吩和呋喃化合物.该合成策略同样适用于合成苯并呋喃和苯并噻吩化合物,通过末端炔与邻氟碘苯的Sonogashira偶联反应,然后硫化钠(或氢氧化钾)参与碳氟键的水解和环化反应得到相应的苯并噻吩和苯并呋喃化合物.该合成方法具有反应条件温和、操作简便和高产率等优点,可为该类呋喃和噻吩的合成提供简便的途径.
Thiophene and furan derivatives are the core skeletons of many natural products, pharmaceuticals and luminescent materials. Therefore, it is of great importance to develop a method for efficient synthesis of furan and thiophene derivatives from simple and easy-to-use raw materials. Synthesis of 2,5-disubstituted furan, 2,5-disubstituted thiophene, benzofuran and benzothiophene compounds in high yields was achieved by first synthesis of 1,4-disubstituted diacetylene by copper-catalyzed terminal alkyne Glaser coupling reaction Compounds, followed by sodium sulfide (potassium hydroxide) participate in the hydrolysis and cyclization reaction to give 2,5-disubstituted thiophene and furan compounds.The synthesis strategy is also suitable for the synthesis of benzofuran and benzothiophene compounds, Sonogashira coupling reaction of iodobenzene, and then sodium sulfide (or potassium hydroxide) is involved in the hydrolysis and cyclization reaction of the carbon fluorine bond to obtain the corresponding benzothiophene and benzofuran compounds. The synthesis method has the advantages of mild reaction conditions, simple and convenient operation, High yield, etc., for the synthesis of such furan and thiophene provide a simple way.