A class of catechol derivatives and preparation method thereof

Abstract

The invention discloses a pyrocatechol derivative and a preparation method of the derivative. The preparation method of the derivative comprises the following steps of: (1) taking an aryl phenol compound as a substrate, and 2-chlorine-5-nitryl pyrimidine as an orienting group, slowly adding a redistilled tetrahydrofuran solvent ice bath into sodium hydride in the presence of nitrogen for reactionto form a pyrimidine aryl phenol compound intermediate, (2) taking iodobenzene diacetate as an oxidant and palladium acetate as a catalyst, catalyzing the pyrimidine aryl phenol compound intermediatefor C-H activating reaction in a solvent, performing swab-off, and chromatographic separation and purification to form an acetoxylated phenylamine derivative, and (3) allowing the acetoxylated phenylamine derivative to react in a tetrahydrofuran solvent by using hydrazine hydrate, and performing quenching, washing, extraction, drying, swab-off, and chromatographic separation and purification to form an ortho-aminophenol derivative. The first two steps of the method can be achieved in a pot, and small-scale production of above a 'gram' level can be even achieved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a class of catechol derivatives and a preparation method thereof. Background technique [0002] In recent years, with the rise of transition metal-catalyzed C–H bond functionalization, directing groups assist C sp2 -H bond functionalization has attracted extensive attention. Various directing groups such as amines, imines, oximes, diazenes, amides, pyridines, pyrimidines, carboxylic acids, etc., were used to achieve regioselective C–H functionalization. Although the introduction and removal of the introducing group usually adds two steps to the overall synthesis, it can become more manipulable if the directing group (DG) is only briefly attached to the substrate molecule during the functionalization step. However, only very limited success examples have been obtained, and only a few reports have been recorded, and the substrates are limited to amines and formaldehy...

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Problems solved by technology

It has been reported in many literatures that the introduction of DG is relatively easy, but the conditions for removing DG are quite harsh. For example, these conditions generally require the use of particularly active metals such as sodium or potassium, and they are still under high temperature conditions. In these literatures, a lot of risk factors have been subtly added to the experiment. What is more serious is that the conditions of these reactions are difficult to achieve in the stage of mass production in practical application. If the company follows this traditional old method to In terms of operation, even small batches of gram-level reactions are difficult to achieve

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