氮芳基取代靛红的合成研究

Synthesis of N-aryl substituted isatin

以靛红、芳基硼酸化合物为原料,经过Ullmann反应,合成了6个含有大体系的氮芳基取代的靛红衍生物.合成化合物的结构运用核磁共振氢谱、碳谱、红外光谱、高分辨质谱的技术手段进行了表征,为进一步研究靛红衍生物的光学性质及生物活性奠定了一定的物质基础.进一步研究发现,在Ullmann反应条件下,靛红能发生自身缩合反应.芳基硼酸能被铜试剂氧化生成1,2-二羰基化合物.

Six nitrogen-substituted isatin derivatives bearing a large-conjugated system were synthesized through Ullmann reaction with isatin and arylboronic acid compounds as substrates.These compounds were characterized by 1H NMR,13C NMR,IR and HRMS.It provides a solid base for further investigation of optimal properties and biological activities of these isatin compounds.Further investigation found that condensation reaction took place with isatin under Ullmann reaction conditions.And arylboronic acid 5c was oxidized by Cu(OAc)2 to afford the byproduct 8.