Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 694-703.DOI: 10.6023/cjoc201909009 Previous Articles     Next Articles


赵宇, 王卫伟, 刘鑫磊, 耿瑞, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2019-09-06 修回日期:2019-10-11 发布日期:2019-11-07
  • 通讯作者: 王明安
  • 基金资助:

Catalyst-Free Domino Reaction of Ethyl 4-Hydroxyalkyl-2-ynoate with N-Heteroarylmethyl-N-2,2-difluoroethan-1-amine

Zhao Yu, Wang Weiwei, Liu Xinlei, Geng Rui, Wang Ming'an   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2019-09-06 Revised:2019-10-11 Published:2019-11-07
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21772229).

The catalyst-free domino reaction of ethyl 4-hydroxyalkyl-2-ynoate and N-heteroaryl-methyl-N-2,2-difluoroethan-1-amine was developed, and used to synthesize 4-(N-(2,2-difluoroethyl)(N-heteroarylmethyl)amino)-5,5-disubstitutedfuran-2(5H)-one in methanol under the reflux condition with yields of 39%~83%. Their structures were characterized by 1H NMR, 13C NMR, and HR-ESI-MS data, further confirmed by the X-ray crystal diffraction of 3-chloro-4-((N-2,2-difluoroethyl)(N-pyrimidin-5-ylmethyl)amino)-5,5-spiro(4-methoxycyclohexyl)furan-2(5H)-one (8). The bioassay results showed that 4-((N-2,2-difluoroethyl)(N-6-chloropyridin-3-ylmethyl)amino)-5,5-dimethylfuran-2(5H)-one (3a) and 4-((N-2,2-difluoroethyl)(N-6-fluoropyridin-3-ylmethyl)-amino)-5,5-dimethylfuran-2(5H)-one (3c) exhibit 100% mortality against Myzus persicae at the concentration of 600 μg·mL-1, respectively.

Key words: 5,5-disubstitutedfuran-2(5H)-one, domino reaction, addition-lactonization, insecticidal activity