摘 要：以四氟对苯二甲腈和各种亲核试剂为原料, 研究了温和条件下的成环反应，生成了一系列含氟杂环化合物。四氟对苯二甲腈与乙二胺在室温下，以DMF为溶剂，超声反应5 min，得到6,7-二氟-1,2,3,4-四氢喹喔啉-5,8-二甲腈 (b)，收率达75%。在同样条件下，进一步考察了其它亲核试剂，例如1,2-丙二胺、邻苯二酚、2,3-二羟基萘、3,4-甲苯二硫醇、1,2-环己二胺、N-甲基乙二胺、N-苯基乙二胺等的反应活性。产物经IR、1H NMR、13C NMR、MS、X-衍射、UV等分析，证明所合成产物结构与预期结构相符。另外，测试了产物的荧光性质，以化合物b为例， 其最大吸收波长为436 nm，最大发射波长为498 nm，具有潜在的应用价值 。
关键词：四氟对苯二甲腈；亲核成环反应；杂环化合物；超声合成；荧光
Abstract: A simple and efficient synthesis of fluorine-containing heterocycles via SNAr reaction of tetrafluoroterephthalonitrile with various nucleophiles assisted by ultrasound has been developed. For example, the reaction between ethylenediamine and tetrafluoroterephthalonitrile proceeded smoothly at room temperature within 5 minutes in DMF to afford product b in 75% yield. Other nucleophiles such as 1,2-diaminopropane, catechol, 2,3-dihydroxynaphthalene, 3,4-dimercaptotoluene, cis-1,2-diaminocyclohexane, N-Methylethylenediamine, N-phenylethylenediamine were also investigated under the optimized conditions. The products were determined by IR, 1H NMR, 13C NMR, MS, X-diffraction analysis and UV analysis and the structures were identified with the expected structures. Moreover, the fluorescence properties of the products were tested. Using compound b as example, the maximum absorption wavelength and the maximum emission wavelength h are 436 nm and 498 nm, respectively, which showing potential application prospect.
Key words: tetrafluoroterephthalonitrile; nucleophilic cyclization; heterocycles; ultrasound irradiation; Fluorescence
