Arylacridine derivatives synthesized under palladium catalysis and preparation method thereof

Abstract

The invention discloses arylacridine derivatives synthesized under palladium catalysis and a preparation method thereof. The arylacridine derivatives are prepared through a reaction with 2-(arylamino)benzonitrile derivatives and aryl boric acid as reactants. According to the invention, the reactants are wide in source; preparation is easy; the arylacridine derivative is low in cost and toxicity and difficultly affects human health; the reaction is carried out in a solvent which is water; during the reaction, a palladium catalyst, an additive and a ligand are also added into the solvent, wherein the palladium catalyst is any one selected from the group consisting of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate, and the additive is methanesulfonic acid; a reaction temperature is 90-110 DEG C, and reaction time is 20-25 h; and the whole reaction is carried out in air, the reaction conditions are very mild, easy to realize and safe, and the health of experimenters is guaranteed. The highest yield of the method can reach 94%; a series of the arylacridine derivatives can be prepared; and the method has high substrate universality and isworthy of popularization.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an aryl acridine derivative synthesized by palladium catalysis and a preparation method thereof. Background technique [0002] Arylacridine and its derivatives are an important class of organic compounds, which have great application value and broad application prospects in the fields of biomedicine, food, cosmetics and organic electronic materials. [0003] In the prior art, aryl acridine and derivatives thereof are mainly prepared by the following methods: 1. Carrying out cyclization reaction of palladium catalyzed 2-aminobenzophenone and cyclohexanone to prepare aryl acridine derivatives ( Eur.J.Org.Chem.2017,577-581); 2. Using 9-chloroacridine and arylboronic acid as raw materials, at 100°C, using toluene as a solvent, the arylacridine compound was prepared by substitution reaction (Chem. Commun. 2017, 53, 13063). However, there are certain defects in the above-mentioned me...

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Problems solved by technology

However, there are certain defects in the above-mentioned methods. Among them, the reaction conditions of method 1 are very harsh, and it needs to be carried out under an oxygen atmosphere at 160 ° C, and the solvent used is TCE. TCE is a toxic solvent, and low-dose inhalation may alcohol-like intoxication

And method 2 needs to use poisonous POCl when synthesizing 9-chloroacridine 3 or SOCl 2 , both of which have pungent odor and certain toxicity, are likely to affect the health of experimenters, and the reaction is relatively dangerous, which is not in line with the development of green chemistry; due to the existence of these defects, the practicability and applicability of these methods Sex has been greatly restricted and cannot be promoted on a large scale

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