A kind of preparation method of the aryl acridine derivative synthesized by palladium catalysis

Abstract

The invention discloses an arylacridine derivative synthesized by palladium catalysis and a preparation method thereof, which is prepared by reacting 2-(arylamino)benzonitrile derivatives and arylboronic acid as reactants; the reactants have a wide range of sources, The preparation is easy, the cost is low, and the toxicity is low at the same time, and it is difficult to affect human health. The reaction is carried out in a solvent, and the solvent is water; during the reaction, a palladium catalyst, an additive and a ligand are also added to the solvent; the palladium catalyst is any one of palladium chloride, palladium acetate, palladium trifluoroacetate and palladium acetylacetonate One, the additive is methanesulfonic acid; the reaction temperature is 90-110°C, the reaction time is 20-25 hours, the whole reaction is carried out in the air, the reaction conditions are very mild, easy to achieve, and safe, ensuring the health of the experimenters. The yield of the invention can reach up to 94%, and a series of aryl acridine derivatives can be prepared. The method has strong substrate universality and can be popularized.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing aryl acridine derivatives synthesized by palladium catalysis. 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 methods. Among...

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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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