Pyrimidine-Core Extended π-Systems: General Synthesis and Interesting Fluorescent Properties
作者:Kenichiro Itami、Daisuke Yamazaki、Jun-ichi Yoshida
DOI:10.1021/ja044923w
日期:2004.12.1
We have developed a simple but powerful synthetic strategy that permits the assembly of pi-systems onto a pyrimidine core in a programmable and diversity-oriented format. The nucleophilic addition of ArLi to 2-methylthiopyrimidine, followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation, resulted in the production of 4-aryl-2-methylthiopyrimidines. The iterative reaction sequence then
我们开发了一种简单但功能强大的合成策略,允许以可编程和面向多样性的格式将 pi 系统组装到嘧啶核上。ArLi 与 2-甲基硫代嘧啶的亲核加成,然后是 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 氧化,产生 4-芳基-2-甲基硫代嘧啶。然后重复反应序列得到4,6-二芳基-2-甲基硫代嘧啶。在NiCl 2 (dppe)的催化作用下,所得加合物进一步与ArMgBr反应,得到2,4,6-三芳基嘧啶。通过遵循这种合成方案,有趣的嘧啶核 pi 系统以可编程方式快速构建。成功发现了许多有趣的荧光材料和特性(例如,