可见光诱导荧光素钠催化N-芳基四氢异喹啉的交叉脱氢偶联合成THIQs类化合物

Visible Light-induced Cross-dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines to Synthesize THIQs Compounds Catalyzed by Fluorescein Sodium

1,2,3,4-四氢异喹啉类化合物存在于许多天然产品中,是合成生物活性分子的重要活性中间体,在药物和生物合成中受到广泛应用,同时,在有机合成领域中也具有重要的潜在应用价值。在以2-位芳环上连有不同取代基的N-芳烃四氢异喹啉类化合物(1a~1n)为原料,以12 W蓝色LED灯为光源,荧光素钠为光催化剂,甲醇为溶剂的最佳反应条件下,于室温反应8 h,合成了14个带有不同取代基的2-位(芳基)-1,2,3,4-四氢异喹啉类化合物(2a~2n),产率可达82%~96%,其结构通过^(1)H NMR和^(13)C NMR表征,并分析了反应可能的机理。该方法具有方便高效、环境友好、原子经济和产率较高的特点。

1,2,3,4-tetrahydroisoquinolines are found in many natural products and are important active intermediates in the synthesis of bioactive molecules,which are widely used in pharmaceutical and biosynthesis.Also,they have vast potential applications in the field of organic synthesis.N-aryl tetrahydroisoquinolines with different substituents attached to the aromatic ring at the 2-position(1a~1n)were used as raw materials,fourteen 2(aryl)-1,2,3,4-tetrahydroisoquinolines with different substituents(2a~2n)were synthesized under the optimum conditions of 12 W blue LED lamp as light source,sodium fluorescein as photocatalyst,methanol as solvent,at room temperature and air for 8 hours.The yield of these target products reached 82%~96%.The structures of products were characterized by ^(1)H NMR and ^(13)C NMR,and the possible mechanism of the reaction was analyzed.This method shows the characteristics of convenient,efficient,environmentally friendly,atomic economy,and high yield.