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 |
| |
引用本文: | 赵宇,王卫伟,刘鑫磊,耿瑞,王明安.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[J].有机化学,2020(3):694-703. |
| |
作者姓名: | 赵宇 王卫伟 刘鑫磊 耿瑞 王明安 |
| |
作者单位: | 中国农业大学应用化学系 |
| |
基金项目: | 国家自然科学基金(No.21772229)资助项目. |
| |
摘 要: | 开发了无催化剂条件下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.应用该反应在甲醇中回流,以39%~83%的收率合成了一系列4-(N-(2,2-二氟乙基)(N-杂环芳基甲基)氨基)-5,5-二取代呋喃-2(5H)-酮,其结构经1H NMR,13C NMR和HR-ESI-MS表征,并进一步通过3-氯-4-(N-2,2-二氟乙基)(N-嘧啶-5-基甲基胺基)-5,5-螺(4-甲氧基环己基)呋喃-2(5H)-酮(8)的晶体衍射间接证实.测试了所合成化合物的生物活性,结果表明,在600μg·mL^-1浓度时4-(N-2,2-二氟乙基)(N-6-氯吡啶-3-基甲基胺基)-5,5-二甲基呋喃-2(5H)-酮(3a)和4-(N-2,2-二.氟乙基)(N-6-氟吡啶-3-基甲基胺基)-5,5-二甲基呋喃-2(5H)-酮(3c)对桃蚜的死亡率均为100%.
|
关 键 词: | 5 5-二取代呋喃-2(5H)-酮 串联反应 加成-内酯化反应 杀虫活性 |
Catalyst-Free Domino Reaction of Ethyl 4-Hydroxyalkyl-2-ynoate with N-Heteroarylmethyl-N-2,2-difluoroethan-1-amine |
| |
Institution: | (Department of Applied Chemistry,China Agricultural University,Beijing 100193) |
| |
Abstract: | The catalyst-free domino reaction of ethyl 4-hydroxyalkyl-2-ynoate and N-heteroaryl-methyl-N-2,2-difluoroethan1-amine was developed,and used to synthesize 4-(N-(2,2-difluoroethyl)(N-heteroarylmethyl)amino)-5,5-disubstitutedfuran2(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-difluoroethy1)(N-6-chloropyridin-3-ylmethyl)amino)-5,5-dimethylfuran-2(5H)-one(3a)and 4-((N-2,2-difluoroethy1)(N-6-fluoropyridin-3-ylmethyl)-amino)-5,5-dimethylfuran-2(5H)-one(3c)exhibit 100%mortality against Myzus persicae at the concentration of 600μg·mL^-1,respectively. |
| |
Keywords: | 5 5-disubstitutedfuran-2(5H)-one domino reaction addition-lactonization insecticidal activity |
本文献已被 维普 等数据库收录! |
|