5-acetyl-4-(n-substituted carbazolyl)-6-methyl-3,4-dihydropyrimidin-2-one and its preparation method

Abstract

In a dry three-necked flask, add A mol of choline chloride, B mol of methanesulfonic acid, stir at room temperature to obtain a deep eutectic solvent, then add C mol 3-formyl-9-alkylcarbazole, D mol urea React with E mol acetylacetone in a water bath at 50°C, and monitor by TLC until the reaction is complete. After the reaction, the reaction solution was poured into water to precipitate a solid, which was suction filtered, washed and dried to obtain a crude product, and the filtrate was recovered to obtain a deep eutectic solvent again. The crude product was recrystallized from absolute ethanol to obtain pure 5-acetyl-4-(N-substituted carbazolyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one. The invention has the advantages of simple operation, high yield, high product purity, short reaction time, and the deep eutectic solvent can be recycled and reused, which is environmentally friendly and low in cost, which is of great significance to the synthesis and development of this type of compound.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of 5-acetyl-4-(N-substituted carbazolyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one. Background technique [0002] Dihydropyrimidinones are a very important class of nitrogen-containing heterocyclic compounds, which have been found to have potential in biology, pharmacology and materials science. One of the most important is as a pharmaceutical intermediate. Dihydropyrimidinone can be used as a lead in the development of anticancer drugs, urease inhibitors, antimalarial agents, calcium channel antagonists, etc., and has antiviral, antifungal, antitumor, and antiinflammatory effects. Due to its broad application prospects, the synthesis of dihydropyrimidinones has also attracted great attention from researchers. [0003] At present, the synthesis of dihydropyrimidinones by the Biginelli reaction is the most important method. The traditional synthesis method h...

AI Technical Summary

Problems solved by technology

The traditional synthesis method has low yield and long reaction time, and many new technologies are also applied to the synthesis, such as microwave and ultrasonic assisted reaction, using new catalysts such as heteropolyacids, ionic liquids, polymer nanomaterials, etc., although it can improve the production rate. efficiency, but there are also problems such as harsh reaction conditions, expensive catalysts, and high toxicity

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