Method for preparing 3-formacyl chromone derivative

Abstract

The invention relates to a 3-formacyl chromone derivative preparing method, making bis(trichloromethyl) carbonate fully react with N,N-dimethylformamide in C1-C4 halogenated hydrocarbon solvent at 0-5 deg.C, then adding in C1-C4 halogenated hydrocarbon solution of 2-hydroxy acetophenone derivative, raising temperature to 25-30 deg.C to react for 12-16 hours, separating and purifying the resultant and obtaining the 3-formacyl chromone derivative. And it has advantages of raw materials easy to obtain, reacting conditions moderate, simple and convenient to operate, clean and less pollution, good product purity, and high product yield; and it is a chemical synthesizing method with better spreading application prospect.

Description

(1) Technical field [0001] The invention relates to a preparation method of 3-formyl chromone derivatives. (2) Background technology [0002] The 3-formyl chromone derivative itself has important pharmacological activities such as antibacterial, antiviral, blood lipid lowering, and preventing arrhythmia, and is also a widely used drug intermediate. 3-formyl chromone derivatives have three electron-deficient sites (C-2, C-4, -CH=O), which can react with different types of nucleophiles to obtain a large number of heterocyclic compounds. In the field of pharmaceuticals, the potential pharmacological activity of 3-formylchromone and its functionalized derivatives are used as the preferred active group for the design of various therapeutic drugs such as diabetes and obesity. In the chemical industry, 3-formyl chromone and its derivatives can also be used to synthesize photosensitizers, which are widely used in the image production industry. The 3-heterocyclic substituted chromo...

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Problems solved by technology

[0003] 3-formyl chromone was first prepared by reacting 2-formyl-2'-hydroxyacetophenone with triethyl orthoformate and acetic anhydride, but the yield of this method was very low, and there were many reaction steps, so It has been rarely used; secondly, 3-formyl chromone can also be obtained by Vilsmeier reaction by 2,2-4-methylnaphthyl-1,3,2-dioxaborane derivatives, but the raw materials of this method are less It is difficult to prepare, and the yield is low, so it also has certain limitations; later, Nahara et al. improved the Vilsmeier method, using o-hydroxyacetophenone derivatives as raw materials, and obtained 3-formyl color in one pot. Ketone derivatives

However, there are still certain limitations in the method of Nahara et al., mainly reflected in that the yield of o-hydroxyacetophenone derivatives with different substituents varies greatly, such as for strong electron donating genes (OCH3, OH), strong absorbing Electron genes (such as NO 2 ) substituted o-hydroxyacetophenone derivatives, the yields are all low

Although in recent years, with the gradual development of microwave method and solid-phase synthesis in the field of organic synthesis, some people have also carried out research on this method, and developed microwave-assisted synthesis and solid-phase synthesis of 3-formyl chromone derivatives. However, since these methods are still in the research and exploration stage for organic synthesis, the application still needs a certain amount of time to be perfected.

Therefore, using o-hydroxyacetophenone as a raw material to synthesize 3-formyl chromone derivatives through the Vilsmeier-Hacck reaction is still the most effective method for preparing 3-formyl chromone, and the most commonly used method for preparing Vilsmeier Reagent is POCl 3 and N,N-dimethylformamide, but because organophosphorus pollution is a growing problem at present, scientific and technological workers are also trying to find a method that can replace phosphorus reagents for traditional reactions

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