2-oxazolidinone derivative preparation method

Abstract

The present invention relates to a 2-oxazolidinone derivative preparation method, belongs to the technical field of organic synthesis. The preparation method is as follows: introducing carbon dioxide into primary amine, to obtain ammonium carbamate salt; then mixing the ammonium carbamate salt with a catalyst, a solvent, terminal alkyne and aldehyde; sealing the materials and stirring the materials at 40-120 DEG C for 8-24 h; after completion of the reaction, performing silical gel column chromatography, to obtaining the 2-oxazolidinone derivative, wherein the catalyst is cuprous chloride, cuprous bromide, cuprous iodide, cuprous thiocyanate, copper trifluoromethane sulfonate, cuprous oxide, copper sulfate, copper nitrate, or copper acetate; and the solvent is methanol, ethanol, ethylene glycol, diethylene glycol, isopropanol or N,N-dimethylformamide. According to the preparation method, the carbon dioxide is used as a protection agent of the primary amine and meanwhile as a reactant, and therefore the amount of catalyst is greatly reduced, the reaction efficiency is improved, and the reaction is performed at the atmospheric pressure, so that no oxygen-free operation is needed, the reaction is simple and safe, and the raw materials are cheap and readily available.

Description

technical field [0001] The present invention relates to a kind of preparation method of 2-oxazolidinone (2-oxazolidinone) derivative, specifically, relate to a kind of carbon dioxide (CO 2 ) is fixed as a green synthesis method of 2-oxazolinone derivatives, belonging to the technical field of organic synthesis. Background technique [0002] Since modern times, due to the consumption of a large amount of fossil fuels by human activities, the continuous accumulation of carbon dioxide in the atmosphere has caused a series of environmental problems such as the greenhouse effect and sea level rise. Over the past few years, the fixation and resource utilization of carbon dioxide has attracted widespread attention. In organic synthesis, carbon dioxide can be used as a carboxyl (ester)-based reagent to synthesize high value-added chemicals (T.Sakakura, J.-C.Choi, H.Yasuda, etc.) , Chem.Rev., 2007, 107, 2365-2387; K.Huang, C.-L.Sun, Z.-J.Shi, Chem.Soc.Rev., 2011, 40, 2435-2452; S.N...

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Problems solved by technology

However, the method usually requires reaction conditions such as high temperature and high pressure, and the reaction raw materials need cumbersome synthesis steps and are expensive, and the types of 2-oxazolinone derivatives prepared are very limited

In 2008, Li Chaojun’s research group reported the synthesis of 2-oxazolinone derivatives through the four-component series reaction of cheap and easy-to-obtain terminal alkynes, aldehydes, primary amines, and carbon dioxide. However, the amount of catalyst used in the method is as high as 30 mol%. Limits its application to some extent (Yoo, W.-J.; Li, C.-J., Adv Synth Catal 2008, 350, 1503-1506)

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