University Chemistry ›› 2020, Vol. 35 ›› Issue (4): 90-95.doi: 10.3866/PKU.DXHX201912038

Special Issue: 全国大学生化学实验创新设计竞赛

Previous Articles     Next Articles

Study on the LED Light Induced Cyanomethylation of Imidazopyridine Used in the Teaching of Undergraduate Laboratory Course

Lei Wang, Chuwen Song, Qingyu Gu, Yinghua Zhang, Ping Liu(), Peipei Sun()   

  • Received:2019-12-10 Accepted:2019-12-16 Published:2020-03-04
  • Contact: Ping Liu,Peipei Sun E-mail:pingliu@njnu.edu.cn;sunpeipei@njnu.edu.cn

Abstract:

Visible light-catalyzed organic reactions have the advantages of high efficiency, operational simplicity, low loading of catalysts under mild conditions, and have received much attention in recent years. The compounds based on the skeleton of imidazo[1, 2-a]pyridine show an impressively wide range of biological activities, such as anti-inflammatory, antiviral activity, antiprotozoal agents, inhibitors of cyclin-dependent kinases, etc. 3-Cyanomethyl-2-phenylimidazo[1, 2-a]pyridine is a key intermediates for the synthesis of the antidepressant drug zolpidem. In our previous work, 3-cyanomethyl-2-phenylimidazo[1, 2-a]pyridine was synthesized via a visible light-promoted reaction of 2-phenyl-imidazo[1, 2-a]pyridine with bromoacetonitrile using fac-Ir(ppy)3 as the photocatalyst. Based on the reaction, herein, the new method about visible light-catalysis was applied to laboratory teaching for broadening the horizons of undergraduates and improving their interests on organic chemistry experiments. Meanwhile, it will help the undergraduates master the basic operations of microchemistry experiments and the use of related instruments. Moreover, this experiment meets the requirements of green chemistry, since it is performed under LED lamp radiation in the absence of toxic reagents. This method also features operational simplicity, low cost, high yield, and good repeatability, etc.

Key words: Green chemistry, LED photocatalysis, 3-Cyanomethylated imidazopyridines, Laboratory teaching

MSC2000: 

  • G64