新型吡唑基吡啶衍生物的合成及催化Suzuki偶联反应
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摘要
以4-苯基苯酚和4-叔丁基苯酚为原料设计合成杯芳烃片段桥连的吡唑基吡啶衍生物L1、L2,并采用1H NMR、13C NMR对其结构进行表征。结果表明,化合物L1作为配体,V (DMF)∶V (水)=2:1为溶剂,在80℃时对钯催化Suzuki偶联反应有良好的促进作用。
Two new pyrazolyl pyridine derivatives L1 and L2 connected by calixarene bridge were designed and synthesized by 4-phenyl phenol and 4-tert-butyl phenol. The structure of L1 and L2was ascertained by1 H NMR,13 C NMR. The study showed that L1 could accelerate Suzuki cross-coupling reaction in solvent with V(DMF) ∶ V(水) = 2∶ 1 at 80 ℃.
Two new pyrazolyl pyridine derivatives L1 and L2 connected by calixarene bridge were designed and synthesized by 4-phenyl phenol and 4-tert-butyl phenol. The structure of L1 and L2was ascertained by1 H NMR,13 C NMR. The study showed that L1 could accelerate Suzuki cross-coupling reaction in solvent with V(DMF) ∶ V(水) = 2∶ 1 at 80 ℃.
引文
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[3]谭成侠,傅寅翼,潘丽艳,等.具有杀虫杀瞒活性的毗哩类化合物的研究进展[J].现代农药,2010,9(1):10-14.Tan Chengxian,Fu Yanyi,Pan Liyan,et al.Research progress on the pyrazole derivatives as insecticide and acaricide[J].Modern Agrochemicals,2010,9(1):10-14.
[4]陈伟,关爱莹,杨莉,等.4-氯-1,3-二甲基-N-(2-(6-苯氧基吡啶-3-基)乙基)-1H-吡唑-5-酞胺的合成与生物活性[J].农药,2014,53(5):316-318.Chen Wei,Guan Aiying,Yang Li,et al.The synthesis and biological activity of 4-chloro-1,3-dimethyl-N-(2-(6-phenoxypyridin-3yl)ethyl)-1H-pyrazole-5-carboxamide[J].Agrochemicals,2014,53(5):316-318.
[5]Ye W J,Zhao M,Du W M,et al.Highly active ruthenium(Ⅱ)complex catalysts bearing an unsymmetric;al N N Nnigandinthe(asymmetric)transfer hyrogenation of ketones[J].Chemistry-A European Journal,2011,17:4737-4741.
[6]薛超,伍成城,周越涵,等.2,6-双吡唑基吡啶Cu(II)配合物对环己烯的催化氧化反应[J].湖北大学学报(自然科学版),2017,39(6):668-673.Xue Chao,Wu Chengcheng,Zhou Yuehan,et al.The oxidation of cyclohexene catalyzed by Cu(Ⅱ)complexes with 2,6-bis(pyrazol-3-yl)pyridine ligands[J].Journal of Hubei University(Natural Science Edition),2017,39(6):668-673.
[7]Wang P,Leung C,Ma D,et al.Structure-based design of platinum(II)complexes as c-myc oncogene down-regulators and luminescent probes for g-uadruplex DNA[J].Chemistry-A European Journal,2010,16:6900-6911.
[8]万丽娟,邢娜,万丽英,等.Cd(II)双苯吡唑基吡啶-草酸混配合物的合成、结构与性质[J].应用化学,2012,29(11):1266-1271.Wan Lijuan,Xing Na,Wan Liying,et al.Synthesis,structure and properties of the cadmium complex using bisphenylpyrazolyl-pyridine derivative and oxalate as mixed ligands[J].Chinese Journal of Applied Chemistry,2012,29(11):1266-1271.
[9]郭勋,刘芳,陆国元.杯芳烃衍生物研究进展[J].有机化学,2005,25(9):1021-1028.Guo Xun,Liu Fang,Lu Guoyuan.Recent progress on study of calixarene derivatives[J].Chinese Journal of Organic Chemistry,2005,25(9):1021-1028.
[10]王丹丹,吕早生,徐珍,等.杯[4]芳烃咪唑盐的微波合成及在氟化反应中的应用[J].化学试剂,2017,39(5):471-476.Wang Dandan,Lv Zaosheng,Xu Zhen,et al.Microwaveassisted synthesis of calix[4]arene imidazolium salts and application in fluoridation[J].Chemical Reagents,2017,39(5):471-476.
[11]王小梅,陈平.杯芳烃磺酸催化合成环氧化合物[J].合成化学,2018,26(1):36-41.Wang Xiaomei,Chen Ping.Synthesis of epoxides catalyzed by p-sulfonic acid calixarene[J].Chinese Journal of Synthetic Chemistry,2018,26(1):36-41.
[12]Kuk R Y,Seung,Soo M L,et al.Synthesis and characterization of carbazole derived nonlinear optical dyes[J].Dyes and Pigments,2007,75:567-573.
[13]Kwang H N,Gutsche C D.Calixarenes.8.Short,stepwise synthesis of p-phenylcalix[4]arene and p-phenyl-ptert-butylcalix[4]arene and derived products[J].Journal of Organic Chemistry,1982,47(14):2713-2719.
[14]Noda Y,Kashima M.An efficient and regioselective direct aromatic iodination using iodine and nitrogen dioxideresearch article[J].Tetrahedron Letter,1997,38(31):6225-6228.
[15]黄素玉.吡唑吡啶类钯(II)配合物的合成及其催化Suzuki偶联反应的研究[D].南宁:广西民族大学,2013.