铜催化肟酯与苄醇构建多取代吡啶

doi:10.11944/j.issn.1000-0518.2016.11.160026

摘要/Abstract

摘要：

以肟酯和苄醇为反应物,三氟甲磺酸铜[Cu(OTf)₂]为催化剂,通过“一锅法”反应合成三取代吡啶化合物。分别考察了不同催化剂及其用量、原料配比、溶剂及温度对反应的影响,在最优条件下,反应的收率为85%,目标化合物经核磁共振氢谱、核磁共振碳谱以及质谱进行了结构表征。该方法具有原料易得,操作简单,反应条件简单温和,产物收率高以及底物适用性好等优点。

关键词: 肟酯, 苄醇, 铜催化, 吡啶衍生物, 一锅法

Abstract:

Pyridine derivatives were synthesized in a one-pot reaction from oxime acetates and benzyl alcohols in the presence of copper(Ⅱ) trifluoromethanesulfonate [Cu(OTf)₂] catalyst. The effect of catalysts and their dosage, raw material ratios, solvents, and temperatures on the yield were investigated. The target compound 2,4,6-trisubstituted pyridine was obtained in 88% yield under the optimum condition. The molecular structures of products were analyzed by mass spectrometry and nuclear magnetic resonance spectroscopy(¹H NMR and ¹³C NMR). The method has several advantages:commerically available materials, easy operation, mild reaction conditions, good yields and a wide range of functional group tolerance.

Key words: oxime acetate, benzyl alcohol, copper-catalyzed, pyridine derivative, one-pot reaction

石赟, 任超杰, 张宁. 铜催化肟酯与苄醇构建多取代吡啶[J]. 应用化学, 2016, 33(11): 1289-1294.

SHI Yun, REN Chaojie, ZHANG Ning. Synthesis of Pyridines via Copper-catalyzed Reaction of Oxime Acetates with Benzyl Alcohols[J]. Chinese Journal of Applied Chemistry, 2016, 33(11): 1289-1294.

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