Chromon-substituted 2-hydroxypyrrole derivatives, and synthesis method and application thereof

Abstract

The invention discloses chromon-substituted 2-hydroxypyrrole derivatives, and a synthesis method and an application thereof, and belongs to the technical field of medicinal chemistry. The structural formula of the chromon-substituted 2-hydroxypyrrole derivatives is shown in the description; and in the formula, n is 0 or 1, R is hydrogen, fluorine, chlorine or a methyl group, R<1> is hydrogen or fluorine, R<2> is hydrogen, fluorine, chlorine or bromine, and EWG is a benzoyl group, a p-methylbenzoyl group, a p-fluorobenzoyl group, a p-chlorobenzoyl group or a p-bromobenzoyl group. The target compounds with an anti-inflammatory activity, which are the chromon-substituted 2-hydroxypyrrole derivatives, are prepared from benzoylformaldehyde derivatives, coumarin derivatives and heterocyclic ketene aminals through a one-pot cascade reaction. The method has the advantages of easily available synthesis raw materials, simple synthesis process, no metal catalyst in the reaction, and low synthesis cost, and realizes the catalyst-free, simple and efficient one-pot process synthesis of the complex and diverse chromon-substituted 2-hydroxypyrrole derivatives.

Description

technical field [0001] The invention relates to 2-hydroxypyrrole derivatives substituted by chromone groups and their synthesis methods and applications, belonging to the technical field of medicinal chemistry. Background technique [0002] Pyrroles are widely found in natural products and bioactive molecules. Pyrrole derivatives are widely used in anti-inflammatory, antiemetic, antihypertensive, antidepressant, treatment of migraine, antitumor and other fields. For example, hydroxypyrrole has anti-inflammatory, anti-bacterial, anti-microbial, anti-tumor, anti-depressant and lower blood pressure and heart rate effects. So far, chemical and pharmaceutical scientists have established various synthetic methods and synthesized a large number of pyrrole compounds. From the perspective of constructing the pyrrole skeleton, these synthetic methods mainly include Hantzsch, Knorr, Paal-Knorr, Barton-Zard, Huisgen method, cyclization, cycloaddition, transition metal catalyzed C-H bo...

AI Technical Summary

Problems solved by technology

The pyrrole compounds synthesized by existing methods are usually pyrrole compounds with simple structure, but the synthesis of 2-hydroxypyrrole derivatives is more difficult or the method for synthesizing such derivatives usually requires relatively harsh conditions

In particular, the synthesis of highly functionalized 2-hydroxypyrrole derivatives, such as chromone-substituted 2-hydroxypyrrole compounds, has not been reported yet

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