Citation: Zhao Yu, Wang Weiwei, Liu Xinlei, Geng Rui, Wang Ming'an. Catalyst-Free Domino Reaction of Ethyl 4-Hydroxyalkyl-2-ynoate with N-Heteroarylmethyl-N-2, 2-difluoroethan-1-amine[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 694-703. doi: 10.6023/cjoc201909009 shu

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

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Received Date: 6 September 2019
Revised Date: 11 October 2019
Available Online: 17 November 2019
Fund Project: the National Natural Science Foundation of China 21772229Project supported by the National Natural Science Foundation of China (No. 21772229)

Figures(5)

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.
- 5, 5-disubstitutedfuran-2(5H)-one,
- domino reaction,
- addition-lactonization,
- insecticidal activity
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