Synthesis method for ortho amino aromatic formic acid aryl ester derivatives

Abstract

The invention discloses a synthesis method for ortho amino aromatic formic acid aryl ester derivatives as shown in the constitutional formula (I). The method includes steps of utilizing isatoic anhydride compound as shown in the constitutional formula (II) and aryl boric acid as shown in the constitutional formula (III) as raw materials to sufficiently react in inertial organic solvent in the presence of palladium catalyst, phosphine ligands and alkaline compounds, and then obtaining the ortho amino aromatic formic acid aryl ester derivatives by means of separation and purification of reaction liquid after reaction. The palladium catalyst includes one or a combination of the following palladiums: palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, dichloro-bis (triphenylphosphine) palladium and dichloro-bis (acetylacetonate) palladium. The synthesis method for the ortho amino aromatic formic acid aryl ester derivatives has the advantages of reasonable technology, low toxicity, mild reaction condition, high reaction yield and fine product quality.

Description

(1) Technical field The present invention relates to a kind of chemical synthesis method of the aryl anthranilate derivative as shown in formula (I). (2) Background technology Aryl anthranilate compounds are a class of compounds with good biological and pharmacological activities, and are widely used in the synthesis of natural products and active drug molecules. Recent studies have shown that this class of compounds also plays an active role in the field of photochemistry. In the prior art, it is more common to synthesize ortho Aryl amino aryl carboxylate derivatives. However, these two methods usually require the reaction to be carried out under strong acid or basic conditions, and the functional group compatibility of the reaction is not very good. Another method is to use the Baeyer-Villiger oxidative rearrangement reaction (such as Synlett 1999, 462 and Synthesis 1991, 739). The selectivity of this method depends on the difference of the substituents on both sides o...

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Problems solved by technology

However, these two methods usually require the reaction to be carried out under strong acid or basic conditions, and the functional group compatibility of the reaction is not very good.

Another method is to use the Baeyer-Villiger oxidative rearrangement reaction (such as Synlett 1999, 462 and Synthesis 1991, 739). The selectivity of this method depends on the difference of the substituents on both sides of the carbonyl group and has high selectivity. However, for the adjacent amino group For aryl formate compounds, the substituents on both sides are aryl groups, so they show similar properties, resulting in extremely low reaction selectivity when the group migrates.

Therefore, the generalization of these methods mentioned above is limited