Synthesis method of benzoxazin ketone compound

Abstract

A synthesis method of a 2-substituted benzoxazin ketone compound shown in the chemical formula (I) comprises the following steps: using 2-aryl indole as a raw material, using potassium hydrogen sulfate compound salt 2KHSO5. KHSO4. K2SO4 oxidation as an oxidizing agent, and performing oxidation reaction to obtain the 2-substituted benzoxazin ketone compound, wherein R represents a hydrogen atom, an alkyl of C1-C6, a naphthenic base, an alkoxy of C1-C6, halogen and an aryl group, and R' represents an aryl group or a substituted aryl group, an alkoxy of C1-C6, an aryloxy group, an alkoxy group of C1-C6 and an aryl amine group. The synthesis method has the advantages of green, high efficiency, mild reaction condition, simple operation, wide application range, low manufacturing cost, high synthesis yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of 2-substituted benzoxazinone compounds, belonging to the technical field of organic synthesis. Background technique [0002] In the modern pharmaceutical and pesticide industries, 2-substituted benzoxazinones are widely used in the preparation of organic heterocyclic intermediates and the synthesis of drugs. In medicine, 2-substituted benzoxazinone itself has important biological and pharmaceutical activities, such as antibacterial, antiviral, anticancer, etc., and it is also an important pharmacophore, which can be used as chymotrypsin, HSV- 1 Inhibitors of protease, serine proteases, human leukocyte elastase, cathepsin G and human chymase, etc. It is worth mentioning that 2-substituted benzoxazinone compounds can also be used as useful intermediates in organic synthesis to prepare quinazolones with a wider range of drug activities, which greatly expands their application in drug synthesis. application. ...

AI Technical Summary

Problems solved by technology

However, the traditional synthesis of 2-substituted benzoxazinones has disadvantages such as harsh reaction conditions, high cost of catalysts or oxidants, limited range of substrates, low yields, and unsuitability for large-scale production. In the past ten years, the synthetic method of 2-substituted benzoxazinone compounds has always been a hot spot and difficult point in the field of organic synthesis. The methods can be summarized into three categories: 1. anthranilic acid and its derivatives or isatoic anhydride and Cyclization reactions of its analogues; 2. Palladium-catalyzed carbonylation reactions; 3. Transition metal-catalyzed cyclization reactions

However, these methods are not in line with the development direction of green chemistry, and the reagents used are highly toxic, expensive, serious environmental pollution, strong corrosion to equipment, and difficult to prepare raw materials.

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