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2024 , Vol. 44 >Issue 5: 1649 - 1657

DOI: https://doi.org/10.6023/cjoc202309009

研究论文

水介质中活性二氧化锰促进2-氨基苄醇与β-二羰基化合物反应合成喹啉衍生物

  • 王义洪 ,
  • 李文丽 ,
  • 林海禄 ,
  • 乐长高 ,
  • 谢宗波
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  • 东华理工大学 江西省合成化学重点实验室 南昌 330013

收稿日期: 2023-09-11

  修回日期: 2023-11-12

  网络出版日期: 2024-01-12

基金资助

江西省自然科学基金(20212ACB203001); 江西省科技创新基地计划(20202BCD42001)

收起

Reaction of 2-Aminobenzyl Alcohols with β-Dicarbonyl Compounds to Synthesize Quinoline Derivatives in Water Promoted by Active Manganese Dioxide

  • Yihong Wang ,
  • Wenli Li ,
  • Hailu Lin ,
  • Zhanggao Le ,
  • Zongbo Xie
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  • Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013
*E-mail: ;

Received date: 2023-09-11

  Revised date: 2023-11-12

  Online published: 2024-01-12

Supported by

Natural Science Foundation of Jiangxi Province(20212ACB203001); Science and Technology Innovation Base Planning Project of Jiangxi Province(20202BCD42001)

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摘要

喹啉及其衍生物在农业、医药等领域被广泛应用, 有关它的高效合成方法备受研究者的关注. 报道了一种在水中2-氨基苄醇和β-二羰基化合物合成喹啉衍生物的简单方法, 在活性二氧化锰和空气存在下该反应很容易进行. 底物范围广, 官能团兼容性好. 此外, 水介质中2-氨基苄醇与苯乙酮反应也可以合成相应的喹啉产物, 但需要氢氧化胆碱和活性二氧化锰作为添加剂, 并在50 ℃加热. 这种方法避免使用昂贵且不稳定的醛, 同时以水作为溶剂, 反应过程变得更绿色、经济.

关键词： 喹啉衍生物; 2-氨基苄醇; 活性二氧化锰; 酮; 水

本文引用格式

王义洪 , 李文丽 , 林海禄 , 乐长高 , 谢宗波 . 水介质中活性二氧化锰促进2-氨基苄醇与β-二羰基化合物反应合成喹啉衍生物[J]. 有机化学, 2024 , 44(5) : 1649 -1657 . DOI: 10.6023/cjoc202309009

Abstract

Quinolines derivatives and their syntheses are of great interest owing to their broad applicability in areas from agriculture to medicine. This paper reports a simple method for the synthesis of quinolines from 2-aminobenzyl alcohols and β-dicarbonyl compounds in water. The reaction was easily performed in the presence of active manganese dioxide in air. A broad substrate scope with good functional group tolerance was observed. Furthermore, the corresponding quinoline products can also be obtained from 2-aminophenyl alcohols and acetophenone in water, choline hydroxide and active manganese dioxide as additives and heating at 50 ℃ are required. The method avoids the use of expensive and unstable aldehydes, and uses water as the solvent, making the process more economical and efficient.

Key words： quinolinone derivative; 2-aminobenzyl alcohol; active manganese dioxide; ketone; water

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