吖啶作为辅助配体的N-杂环卡宾-钯(Ⅱ)化合物:合成、表征和催化应用
收稿日期: 2017-01-19
修回日期: 2017-03-02
网络出版日期: 2017-03-08
基金资助
国家自然科学基金（Nos.U1404205，21572126，21202095）、河南省高校科技创新人才计划（No.14HASTIT016）和河南省重点科技攻关（No.152102410056）资助项目.
N-Heterocyclic Carbene-Palladium(Ⅱ) Complexes with Acridine Ligand:Synthesis, Characterization and Catalytic Applications
Received date: 2017-01-19
Revised date: 2017-03-02
Online published: 2017-03-08
Supported by
Project supported by the National Natural Sciences Foundation of China (Nos.U1404205,21572126 and 21202095),the Program for Science&Technology Innovation Talents in Universities of Henan Province (No.14HASTIT016) and the Key Scientific and Technological Project of Henan Province (No.152102410056).
以咪唑鎓盐、氯化钯和吖啶等为起始原料，经一锅法反应方便地合成了两种新颖的N-杂环卡宾-钯（Ⅱ）化合物.新化合物通过1H NMR，13C NMR和元素分析等手段进行了结构表征，结构通过X射线单晶衍射进行了确定.此外，所获得的钯（Ⅱ）化合物可以作为芳基或苄基氯化合物与芳基硼酸的Suzuki-Miyaura偶联反应高效催化剂.在优化的反应条件下，所有拓展的底物都能成功地发生反应，并得到较好的收率.
关键词： N-杂环卡宾; 钯; 吖啶; Suzuki-Miyaura偶联反应
王涛 , 许凯 , 孟团结 , 张安安 , 王红雨 , 沈思思 , 刘澜涛 . 吖啶作为辅助配体的N-杂环卡宾-钯(Ⅱ)化合物:合成、表征和催化应用[J]. 有机化学, 2017 , 37(7) : 1794 -1799 . DOI: 10.6023/cjoc201701039
Nine new heterozygous isatin-quinazoline compounds were synthesized from cheap and easily available ortho nitrobenzaldehyde as the starting material.The chemical structures of the synthesized compounds were characterized by NMR,IR and HRMS.The structure of (E)-3-(((E)-(5-(4-((3-ethynylphenyl) amino) quinazolin-6-yl) furan-2-yl) methylene) hydrazono)-indolin-2-one (4a) was further determined by crystallization and X-ray diffraction,and the data revealed that its cis-trans isomerism was (E,E).The antitumor activity of these new compounds was evaluated in vitro by methyl thiazolyl tetrazolium (MTT) assay in human colorectal carcinoma cells SW480,human non-small cell lung cancer cells A549 and NCI- H1975,and human epidermoid squamous carcinoma cells A431.The preliminary data demonstrated that most of the synthetic compounds had moderate to potent inhibitory activity against these four tumor cell lines.In particular,compound 4a had highly potent inhibitory activity on proliferation of four cell lines,and the activity was more potent than positive lapatinib.
Key words： N-heterocyclic carbene; palladium; acridine; Suzuki-Miyaura cross-coupling
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