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一种高效且环保的高官能化吡啶酮的合成方法——一锅三组分反应。

An efficient and ecofriendly synthesis of highly functionalized pyridones a one-pot three-component reaction.

作者信息

Hosseini Hajar, Bayat Mohammad

机构信息

Department of Chemistry, Faculty of Science, Imam Khomeini International University Qazvin Iran

出版信息

RSC Adv. 2018 Jul 30;8(48):27131-27143. doi: 10.1039/c8ra05690k.

Abstract

A simple and convenient protocol has been developed for the synthesis of -amino-3-cyano-2-pyridone derivatives by a one-pot reaction of cyanoacetohydrazide, activated nitrile substrates (malononitrile, ethyl cyanoacetate, cyanoacetamide) and aromatic aldehydes in the presence of piperidine in water or a mixture of water and ethanol. The sequence of cascade reactions includes Knoevenagel condensation, Michael addition, intramolecular cyclization, imine-enamine tautomerization and oxidative aromatization. The main advantages of this procedure are availability of starting compounds, simple procedure, mild conditions, easy purification of products and the use of water or water/ethanol as green solvents.

摘要

已经开发出一种简单便捷的方法,通过氰基乙酰肼、活性腈底物(丙二腈、氰基乙酸乙酯、氰基乙酰胺)与芳香醛在哌啶存在下于水或水与乙醇的混合物中进行一锅反应,合成α-氨基-3-氰基-2-吡啶酮衍生物。级联反应的顺序包括克诺文纳格尔缩合、迈克尔加成、分子内环化、亚胺-烯胺互变异构和氧化芳构化。该方法的主要优点是起始化合物易得、步骤简单、条件温和、产物易于纯化以及使用水或水/乙醇作为绿色溶剂。

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