Yu Zhao, Weiwei Wang, Xinlei Liu
2020
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Journal
Chinese Journal of Organic Chemistry
Abstract
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(5 H )-one in methanol under the reflux condition with yields of 39% ~ 83%. Their structures were characterized by 1 H NMR, 13 C 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(5 H )-one ( 8 ). The bioassay results showed that 4-(( N -2,2-difluoroethyl)( N -6-chloropyridin-3-ylmethyl)amino)-5,5-dimethylfuran-2(5 H )-one ( 3a ) and 4-(( N -2,2-difluoroethyl)( N -6-fluoropyridin-3-ylmethyl)-amino)-5,5-dimethylfuran-2(5 H )-one ( 3c ) exhibit 100% mortality against Myzus persicae at the concentration of 600 μ g•mL - 1 , respectively.