| 3-碘-6-卤代咪唑并[1,2-a]吡啶-8-甲酸酯的合成 |
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| 引用本文： | 程伟,杨德亮,张向龙,陈本康,郑爽,张箫壬,袁文鹏.3-碘-6-卤代咪唑并[1,2-a]吡啶-8-甲酸酯的合成[J].化学试剂,2021,43(4):540-545. |
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| 作者姓名： | 程伟 杨德亮 张向龙 陈本康 郑爽 张箫壬 袁文鹏 |
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| 作者单位： | 齐鲁工业大学(山东省科学院)山东省科学院菏泽分院山东省生物工程技术创新中心,山东菏泽274000;山东友帮生化科技有限公司山东省小分子杂环化合物工程实验室,山东菏泽274000 |
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| 基金项目： | 山东省重点研发计划项目(2018CXJJA1060010)。 |
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| 摘 要： | 标题化合物是一类重要杂环化合物,具有较高的生物活性,广泛应用于抗肿瘤药物、抗菌、抗病毒等药物的生产。以2-氨基烟酸为起始原料,经过浓硫酸催化与醇类生成2-氨基烟酸酯,再与N-卤代丁二酰亚胺反应制备2-氨基-5-卤代烟酸酯,再与氯乙醛成环缩合生成6-卤代咪唑并1,2-a]吡啶-8-甲酸酯,最后和N-碘代琥珀酰亚胺发生碘代反应,共4步制得标题化合物,总收率为58.9%~67.7%。产物结构经IR、1HNMR、13CNMR、元素分析进行了表征。合成路线方法新颖、操作简单、产率高、避免柱层析分离纯化,更适合工业化放大生产。
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| 关 键 词： | 2-氨基烟酸 氯乙醛 N-碘代丁二酰亚胺 3-碘-6-卤代咪唑并[1 2-a]吡啶-8-甲酸酯 合成 抗癌药物 |
Synthesis of 3-Iodo-6-haloimidazo [1,2-a] pyridines-8-carboxylic Acid Esters |
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| CHENG Wei,YANG De-liang,ZHANG Xiang-long,CHEN Ben-kang,ZHENG Shuang,ZHANG Xiao-ren,YUAN Wen-peng.Synthesis of 3-Iodo-6-haloimidazo [1,2-a] pyridines-8-carboxylic Acid Esters[J].Chemical Reagents,2021,43(4):540-545. |
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| Authors: | CHENG Wei YANG De-liang ZHANG Xiang-long CHEN Ben-kang ZHENG Shuang ZHANG Xiao-ren YUAN Wen-peng |
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| Affiliation: | (Biological Engineering Technology Innovation Center of Shandong Province,Heze Branch,Qilu University of Technology(Shandong Academy of Sciences),Heze 274000,China;Shandong Engineering Laboratory of Small Molecule Heterocyclic Compounds,Shandong Youbang Biochemical Technology Co.,Ltd.,Heze 274000,China) |
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| Abstract: | The title compounds are important heterocyclic compounds with high biological activity, which can be widely used in the production of anti-cancer drugs, anti-bacterial drugs and anti-virus drugs.In order to explore a new synthetic route, taking 2-aminonicotinic acid as the raw materials, the synthesis gradually went by the following four-step reaction processes with the total yield of 58.9%~67.7%.Reaction with alcohols catalyzed by concentrated sulfuric acid to form 2-aminonicotinic acid esters, halogenation with N-halosuccinimide to form 2-amino-5-halonicotinic acid esters, ring-closing condensation with chloroacetaldehyde, and iodization with NIS to form 3-iodo-6-haloimidazo 1,2-a] pyridines-8-carboxylic acid esters.The structure was confirmed by IR,1HNMR,13CNMR and elemental analysis.The protocol takes the advantages of new synthetic route, easy operation, and high yield, avoiding column chromatography separation and suited for scale-up production. |
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| Keywords: | 2-aminonicotinic acid chloroacetaldehyde N-Iodosuccinimide 3-iodo-6-haloimidazo[1 2-a]pyridines-8-carboxylic acid esters synthesis anti-cancer drugs |
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