Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2743-2749.DOI: 10.6023/cjoc202101015 Previous Articles     Next Articles

ARTICLES

SnCl2@MNPs催化Biginelli反应一锅法合成3,4-二氢嘧啶-2-酮衍生物

赵雯辛a, 黄孟君b, 李胜男a, 刘玉静a, 刘中秋a,*(), 应安国a,b,*()   

  1. a 曲阜师范大学化学与化工学院 山东曲阜 273100
    b 台州学院医药化工学院 浙江台州 318000
  • 收稿日期:2021-01-08 修回日期:2021-02-04 发布日期:2021-04-16
  • 通讯作者: 刘中秋, 应安国
  • 基金资助:
    国家自然科学基金(21978154); 山东省自然科学基金(ZR2020QB191); 曲阜师范大学国家级大学生创新创业训练计划(201910446018)

One-Pot Synthesis of 3,4-Dihydropyrimidine-2-one Derivatives via Biginelli Reactions Catalyzed by SnCl2@MNPs

Wenxin Zhaoa, Mengjun Huangb, Shengnan Lia, Yujing Liua, Zhongqiu Liua(), An'guo Yinga,b()   

  1. a College of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273100
    b College of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, Zhejiang 318000
  • Received:2021-01-08 Revised:2021-02-04 Published:2021-04-16
  • Contact: Zhongqiu Liu, An'guo Ying
  • Supported by:
    National Natural Science Foundation of China(21978154); Natural Science Foundation of Shandong Province(ZR2020QB191); National Students' Platform for Innovation and Entrepreneurship Training Programs(201910446018)

The magnetic Fe3O4 nanoparticles were prepared by a co-precipitation method. The magnetic nanoparticles (MNPs) with core-shell structure were constructed by alkali-catalyzed hydrolysis of tetraethyl orthosilicate, and SnCl2 grafted on MNPs (SnCl2@MNPs) was successfully synthesized by a co-precipitation method. Then the catalyst of SnCl2@MNPs was further analyzed by a series of modern characterization methods for exploring the microstructure and composition. The results showed that SnCl2 was uniformly dispersed on the surfaces of MNPs and there were strong interaction forces between SnCl2 and MNPs. Subsequently, the Biginelli reaction was performed to investigate the catalyst performance, the results showed that 3,4-dihydropyrimidin-2(1H)-ones were efficiently synthesized by a three component one-pot reactions of aromatic aldehydes or heterocyclic aldehydes, carbamide or thiourea, andα,β-dicarbonyl compounds with high yields of 78%~96%. The active fraction of SnCl2 in SnCl2@MNPs is uniformly distributed on the surface of MNPs and in the form of microcrystalline that increases the effective contact area with substrates. The highly activity of SnCl2@MNPs is ascribed to the synergistic effect of SnCl2 and the abundant hydroxyl cluster in MNPs. In addition, the catalyst can be recovered using an external magnetic field and reused at least 7 times without a considerable decrease in its catalytic activity.

Key words: magnetic nanoparticle, Biginelli reaction, aromatic aldehyde, α,β-dicarbonyl compound