摘要/Abstract

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600 μg·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
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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