碱性离子液体催化Friedlander反应合成2,3-二苯基-1,8-萘啶的研究

孙健, 伞影, 谢宁, 金朝辉, 高华晶

现代化工 ›› 2022, Vol. 42 ›› Issue (2) : 167 -171.

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现代化工 ›› 2022, Vol. 42 ›› Issue (2) : 167-171. DOI: 10.16606/j.cnki.issn0253-4320.2022.02.034
科研与开发

碱性离子液体催化Friedlander反应合成2,3-二苯基-1,8-萘啶的研究

    孙健, 伞影, 谢宁, 金朝辉, 高华晶
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Synthesis of 2, 3-diphenyl-1, 8-naphthyridine by Friedlander reaction catalyzed by basic ionic liquids

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摘要

合成了1-丁基-2,3-二甲基咪唑咪唑盐([Bmmim][Im])等6种咪唑类离子液体,并测定了其pH和热分解温度,通过红外光谱(FT-IR)确定了离子液体的结构。将上述离子液体作为溶剂和催化剂分别应用于二苯基乙酮和2-氨基-3-吡啶甲醛的Friedlander反应,考察了底物的摩尔比、反应温度、反应时间等条件对2,3-二苯基-1,8-萘啶收率的影响。结果表明,在以[Bmmim][Im]为催化剂、反应温度为80℃、反应时间为24 h、离子液体用量为5 mL、二苯基乙酮和2-氨基-3-吡啶甲醛摩尔比为1∶0.6的条件下,产品收率可达89.71%,[Bmmim][Im]循环使用4次催化活性没有明显降低。

Abstract

Six types of imidazole ionic liquid, such as 1-butyl-2, 3-dimethyl-1H-imidazol-3-ium imidazol-1-ide ([Bmmim][Im]), are synthesized, their pH values and thermal decomposition temperature are measured, and their structures are confirmed by FT-IR.These ionic liquids are respectively used as solvent and catalyst in the Friedlander reaction between 1, 2-diphenylethan-1-one and 2-aminonicotinaldehyde.The effects of the molar ratio of the substrates, reaction temperature and reaction time on the yield of 2, 3-diphenyl-1, 8-naphthyridine are investigated.The results show that the product yield can reach 89.71% when [Bmmim][Im] is taken as the catalyst, the reaction temperature is at 80℃, the reaction lasts for 24 h, the dosage of ionic liquid is 5 mL, and the molar ratio of 1, 2-diphenylethan-1-one to 2-aminonicotinaldehyde is 1∶0.6.The catalytic activity of [Bmmim][Im] is not significantly reduced after 4 cycles of uses.

关键词

离子液体 / Friedlander反应 / 2,3-二苯基-1,8-萘啶 / 催化

Key words

ionic liquid / Friedlander reaction / 2, 3-diphenyl-1, 8-naphthyridine / catalysis

Author summay

孙健(1984-),男,博士,讲师,主要研究方向为绿色化工与技术,sunjian6225@126.com

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碱性离子液体催化Friedlander反应合成2,3-二苯基-1,8-萘啶的研究[J]. 现代化工, 2022, 42(2): 167-171 DOI:10.16606/j.cnki.issn0253-4320.2022.02.034

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