Catalyst-free method for synthesizing 1,4-diketone compounds

Abstract

The invention discloses a method for synthesizing a 1, 4-diketone compound without a catalyst. In the existence of alkali, the corresponding 1, 4-diketone compound is obtained by reacting silyl enol ether and alpha-haloketone by taking perfluoroalkyl alcohol as a solvent. By adopting the method for synthesizing the 1, 4-diketone compound, the raw materials are easily obtained, the cost is low, the reaction conditions are mild, the operation is simple and easy to control, the side reactions are few, the after-treatment is simple, the product yield is relatively high, and the solvent can be recovered and recycled, so that the production cost is greatly saved; the method has good environment protection benefit and economical benefit and is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to a method for synthesizing 1,4-diketone compounds, in particular to a method for synthesizing 1,4-diketone compounds in one step without a catalyst using alpha-halogenated ketone and enol silicon ether as raw materials. Background technique [0002] 1,4-diketone compound is an important synthetic intermediate through which various carbocyclic and heterocyclic compounds can be synthesized. For example, 1,4-diketone compound can be combined with ammonia, ammonium carbonate, alkyl Many nitrogen-containing compounds such as primary amines can synthesize pyrrole or substituted pyrrole; it can also react with phosphorus pentasulfide to form a thiophene ring; it can synthesize furan under the action of acid; it can synthesize oxime ketone (an intermediate for the synthesis of amino acids). At the same time, many natural products and drug molecules contain 1,4-diketone structures, and some 1,4-diketone compounds can be used as solvents ...

AI Technical Summary

Problems solved by technology

[0003] Although there are many methods for synthesizing 1,4-diketone compounds, these methods have certain limitations, such as difficult to obtain raw materials, limited range of substrates, harsh reaction conditions, low yield, complex and difficult to separate products, Complex post-processing, high production costs, etc.

For example: the most commonly used coupling reaction (DeMartino, M.P.; Chen, K.; Baran, P.S., Intermolecular Enolate Heterocoupling: Scope, Mechanism, and Application.J.Am.Chem. Soc.2008, 130(34), 11546-11560), that is, ketone compounds carry out direct oxidative coupling through enolization, although this method is currently the most simple and convenient way to synthesize 1,4-diketone compounds, but when different When the ketone compound is subjected to oxidative coupling reaction, self-coupling and cross-coupling of the substrate are easy to occur at the same time, resulting in low yield, complicated product and difficult separation. Therefore, this method is mainly suitable for the same kind of ketone compound through itself Oxidative Coupling Synthesis of Symmetrical 1,4-Diketones

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