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

doi:10.6023/cjoc201909009

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

无催化剂条件下4-羟基烷基-2-炔酸乙酯与N-杂环芳基甲基-N-2,2-二氟乙基-1-胺的串联反应

赵宇, 王卫伟, 刘鑫磊, 耿瑞, 王明安

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 E-mail:wangma@cau.edu.cn
基金资助:
国家自然科学基金（No.21772229）资助项目.

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

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).

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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(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

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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.

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无催化剂条件下4-羟基烷基-2-炔酸乙酯与N-杂环芳基甲基-N-2,2-二氟乙基-1-胺的串联反应

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

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