75652-63-0

Usage

Molecular structure

2,4(1H,3H)-Quinazolinedione core with a 3-[2-(4-methoxyphenyl)ethyl] substituent and a methyl group attached to the nitrogen atom.

Classification

Quinazoline derivative.

Methyl group

Attached to the nitrogen atom.

Substituent

3-[2-(4-methoxyphenyl)ethyl] group on the carbon-3 position.

Biological activities

Potential pharmaceutical intermediate with a wide range of biological activities.

Possible applications

Synthesis of various drugs with potential antitumor, antibacterial, or antiviral properties.

Importance of 4-methoxyphenyl group

May contribute to the pharmacological effects of the compound.

Value in medicinal chemistry

A valuable and versatile chemical compound for research and development.

Upstream product

• 79-22-1 methyl chloroformate 
• 75652-61-8 2-methylamino-N-<2'-(4''-methoxyphenyl)ethyl>benzamide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 74-88-4 methyl iodide 
• 847238-29-3 3-(4-methoxyphenethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 118-48-9 isatoic anhydride 
• 55-81-2 4-Methoxyphenethylamine 
• 565171-47-3 2-amino-N-[2-(4-methoxyphenyl)ethyl]benzamide 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 

Relevant academic research and scientific papers

Combining Isocyanides with Carbon Dioxide in Palladium-Catalyzed Heterocycle Synthesis: N3-Substituted Quinazoline-2,4(1H,3H)-diones via a Three-Component Reaction

We report a Pd-catalyzed three-component reaction of 2-bromoanilines, carbon dioxide, and isocyanides. The combination of these two readily available C1-reactants, featuring a huge difference in kinetic and thermodynamic stability, is hitherto unprecedented in transition-metal catalysis. With this one-pot three-component reaction, N3-substituted quinazoline-2,4(1H,3H)-diones are obtained in moderate to high yields in a completely regio- and chemoselective manner. Our approach easily allows variation of the arene and N3-substitution pattern of the desired heterocycle. The formal synthesis of different APIs illustrates its practical applicability. In addition, the methodology also allows for a convenient and selective 13C-labeling through the use of 13CO2. This is illustrated for [2-13C]-2,4-dichloro-6,7-dimethoxyquinazoline synthesis, a key intermediate for several APIs.

Syntheses of quinazoline-2,4-dione alkaloids and analogues from Mexican Zanthoxylum species

Quinazolinone and quinazolinedione derivatives are of considerable interest due to their wide array of pharmacological properties. In this paper we report the synthesis of ten quinazolinediones. The previous isolation of two of these compounds, namely 1-methyl-3-(2′-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[2′-(4′-methoxyphenyl)ethyl]-1H,3H-quinazoline-2,4- dione, from the seed husks of Mexican Zanthoxylum species has been reported.