无金属催化合成3-苯基-4-卤代异喹啉类化合物

Nonmetallic Catalyzed-synthesis of 4-chloroisoquinolines

以邻炔基苄基叠氮和卤盐为原料,利用无金属氟试剂selectfluor作为氧化剂氧化卤盐发生亲电交换反应产生亲电试剂,然后参与叠氮与炔烃的亲电环化反应合成3-苯基-4-氯代异喹啉。实验结果表明:无金属氟试剂selectfluor可以很好的氧化卤盐产生亲电试剂得到产率35%~84%的3-苯基-4-卤代异喹啉类化合物,其结构经~1H NMR,^(13)C NMR和GC-MS表征。该方法反应条件温和、操作简单,并且在产物骨架中引入卤原子,为新官能团的引入提供了途径。

3-chlorophenyl-4-isoquinolines was synthesized through the cycloaddtion reaction of azides and alkynes with o-alkynyl benzyl azide and halide salt as raw material, and on the condition of nonmetal fluoride reagent seleetfluor as the oxidant, it was reacted with halide salt to produce eleetrophilic reagent via electrophilic exchange reactions. The results showed that the metal free fluorine reagent selectfluor can oxidize halide salt to generate a variety of 3-phenylhalide-4- isoquinoline compounds in 35% -84% yields. The structures were confirmed by I H NMR, 13C NMR and GC-MS. This method had many merits such as simple operation and mild reaction condition. Importantly, a halide was introduced into the products which made the methodology more attractive for organic synthesis.