Synthetic method of indanone and derivatives thereof

Abstract

The invention discloses a synthesis method of indanone and derivatives thereof, which comprises the following steps: adding a dialkyl acetylene compound, a palladium catalyst, an additive and an inorganic base into a dry reaction container together, and replacing a gas atmosphere in the reaction container with carbon monoxide from air; adding an o-bromoiodobenzene compound and an anhydrous 1,4-dioxane solvent in a carbon monoxide gas atmosphere, heating to react, and cooling to room temperature; adding a saturated ammonium chloride solution for quenching reaction, adding water, extracting by using ethyl acetate, separating by column chromatography, and purifying to obtain indanone and derivatives thereof. The reaction raw materials are easy to obtain, and the reaction conditions are mild;according to the method, the defects that in a traditional preparation method, the raw materials are complex in structure and not easy to obtain and can be obtained through multiple steps are overcome, carbon monoxide serves as a direct source of carbonyl, three new C-C bonds are built in one reaction, and the method better conforms to the ideas of atom economy, synthesis step economy and green chemistry in organic synthesis.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing indanone and its derivatives through palladium-catalyzed three-molecule series coupling carbonylation reaction. Background technique [0002] Indanone compounds are important intermediates in the synthesis of many natural products, ligands, and material molecules. For example, pauciflorol F, a natural product of polyphenols, can be easily synthesized from indanone compounds. The synthesis of endothelin receptor antagonists SB-209670 and SB-217242 also requires intermediates of indanone structure. In addition, biheterocyclic aryl indanone compounds can undergo reversible conversion under different visible light wavelengths, and are expected to be used as optical braking switches. Therefore, indanone and its derivatives have always been a class of compounds that have attracted the attention of synthetic chemists. In the traditional synthesis...

AI Technical Summary

Problems solved by technology

However, the common feature of these methods is that the substrate needs to be pre-introduced with carbonyl functional group precursors, such as acyl groups, aldehyde groups, etc., so most of them have relatively complex raw materials, which are difficult to commercially purchase and need to be prepared in advance through multi-step reactions

Difficult to achieve large-scale practical application

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