22686-80-2

Basic information

• Product Name: 1-Methyl-2-phenylquinazolin-4(1H)-one
• Synonyms: 1-Methyl-2-phenylquinazolin-4(1H)-one
• CAS NO: 22686-80-2
• Molecular Formula: C₁₅H₁₂N₂O
• Molecular Weight: 236.26858
• Mol File: 22686-80-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Methyl-2-phenylquinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2-phenylquinazolin-4(1H)-one(22686-80-2)
• EPA Substance Registry System: 1-Methyl-2-phenylquinazolin-4(1H)-one(22686-80-2)

Safety Data

• Hazardous Substances Data: 22686-80-2(Hazardous Substances Data)

Usage

Also known as

1-Methyl-2-phenyl-1,2-dihydroquinazolin-4(3H)-one

Type of compound

Heterocyclic compound

Core structure

Quinazolinone

Physical form

Off-white solid

Solubility

Soluble in organic solvents

Pharmaceutical properties

Potential inhibitor of various enzymes and receptors

Use

Building block in the synthesis of various pharmaceutical compounds

Importance

Versatile compound in medicinal chemistry and organic synthesis.

Upstream product

• 10328-92-4 N-Methylisatoic anhydride 
• 100-46-9 benzylamine 
• 56042-78-5 N-benzyl-2-(methylamino)benzamide 
• 1670-14-0 benzamidine monohydrochloride 
• 91-22-5 quinoline 
• 551-93-9 2-aminoacetophenone 
• 69905-99-3 2-methylaminobenzaldehyde oxime 
• 7755-70-6 2-(methylamino)benzaldehyde 
• 3947-76-0 N-methylquinolinium iodide 
• 1010691-01-6 1-(2-(methylamino)phenyl)ethanone oxime 
• 1859-75-2 o-(methylamino)acetophenone 
• 7505-81-9 2-methylaminobenzamide 
• 100-51-6 benzyl alcohol 
• 396716-18-0 N-methyl-N-(2-thiocarbamoyl-phenyl)-benzamide 

Relevant articles and documents

Green synthesis method and application of quinazolinone compound

The invention discloses a green synthesis method and application of a quinazolinone compound. The structure of the quinazolinone compound is shown as a formula I, the preparation method comprises the following steps: by taking an R1-substituted hexafluoroisopropanol 2-aminobenzoate compound and R2-substituted amidine hydrochloride as raw materials, alkali as an additive, and acetonitrile, dioxane, tetrahydrofuran, DMSO (dimethylsulfoxide) or DMF (dimethyl formamide) as a solvent, reacting at normal temperature to generate the quinazolinone compound shown in the formula I. The method provided by the invention has the advantages of no need of heating, no need of using a metal catalyst, mild reaction conditions, no generation of by-products in the reaction, 100% conversion of the raw materials and simple post-treatment process, can be used to obtain the high-purity quinazolinone product, and is a simple green synthesis method; and the quinazolinone compound has high antitumor activity, and can be used for preparing antitumor drugs.

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: A strategy to construct quinazolinones

A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.