香豆素噻唑腙类化合物的合成及其对金属离子识别性能研究

Synthesis of Coumarin Thiazole Hydrazone Compounds and Research on Their Recognition Properties for Metal Ions

在微波辐射条件下,以乙醇为溶剂,无需外加任何催化剂,用3-(2-溴代乙酰基)香豆素、硫脲和芳香族甲醛三组分一锅法合成了12个香豆素噻唑腙类化合物,其中8个化合物是首次报道.反应微波功率为150 W,反应时间15-20 min,产率60%-86%,对合成的新产物进行了熔点、^(1)H NMR、^(13)C NMR和HRMS表征.考察了化合物3g、3j和3l对Cu^(2+)的识别作用,结果显示,化合物3l与Cu^(2+)具有较强的相互作用.考察化合物3l对13种金属离子的识别作用,发现化合物3l对Cu^(2+)、Co^(2+)和Ni^(2+)表现出良好的UV-Vis及裸眼识别能力.滴定实验结果,显示化合物3l与Cu^(2+)形成了1∶1型配合物,3l与Co^(2+)和Ni^(2+)均形成了2∶1型配合物.当pH值为3时,化合物3l可选择性识别Cu^(2+).

Under microwave irradiation,12 coumarin thiazole hydrazone compounds were synthesized by the three-component one-pot reaction of 3-(2-bromoacetyl) coumarin,thiourea and aromatic formaldehyde in ethanol without adding any catalyst,of which 8 compounds were reported for the first time.The microwave power was 150 W,the reaction time was 15-20 min,and the yield was 60%-86%.The new product was characterized by melting point,^(1)H NMR,^(13)C NMR and HRMS.The recognition effects of compounds 3g,3j and 3l on Cu^(2+)were investigated.The results showed that compound 3l had a strong interaction with Cu^(2+).The recognition effects of compound 3l on 13 metal ions were investigated.It was found that compound 3l showed good UV-Vis and naked-eye recognition properties for Cu^(2+),Co^(2+),and Ni^(2+).The titration results showed that compound 3l formed a 1∶1 complex with Cu^(2+)and a 2∶1 complex with Co^(2+)or Ni^(2+).When p H value was 3,compound 3l can selectively recognize Cu^(2+).