2436-66-0

Usage

Uses

Used in Pharmaceutical Research and Drug Discovery:
4(3H)-Quinazolinone, 3-methylis utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and pharmacological properties make it a promising candidate for drug discovery and development, particularly in the areas of anticancer, antiviral, and anti-inflammatory agents.
Used in Organic Synthesis:
In the chemical industry, 4(3H)-Quinazolinone, 3-methylserves as an important building block for the synthesis of a wide range of organic compounds. Its versatile chemical reactivity allows for the formation of various functional groups and derivatives, which can be further utilized in the development of new materials and chemical products.
Used in Medicinal Chemistry:
4(3H)-Quinazolinone, 3-methylis employed as a scaffold in medicinal chemistry for the design and development of novel therapeutic agents. Its ability to interact with various biological targets, such as enzymes, receptors, and nucleic acids, makes it a valuable tool for the discovery of new drugs with improved efficacy and selectivity.
Used in Chemical Research:
4(3H)-Quinazolinone, 3-methylis also used as a model compound in chemical research to study the reactivity, stability, and properties of heterocyclic compounds. Understanding its behavior in various chemical reactions can provide insights into the design of new synthetic routes and the development of innovative applications in the chemical and pharmaceutical fields.

InChI:InChI=1/C9H8N2O/c1-11-6-10-8-5-3-2-4-7(8)9(11)12/h2-6H,1H3

Upstream product

• 64-18-6 formic acid 
• 4141-08-6 2-Amino-N-methylbenzamid 
• 74-89-5 methylamine 
• 1114-38-1 2-ethylbutanamide 
• 28144-70-9 anthranilic acid amide 
• 123-39-7 N-Methylformamide 
• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 4909-78-8 N,N-dimethylformamide dineopentyl acetal 
• 18503-89-4 N,N-dimethylformamide diisopropyl acetal 
• 213211-95-1 3-Methyl-4-oxo-3,4-dihydro-quinazoline-2-carbonitrile 
• 108-98-5 thiophenol 
• 186581-53-3 diazomethane 
• 491-36-1 4-Hydroxyquinazoline 

Downstream Products

• 1213227-12-3 1-[2-(4-nitrophenyl)-2-oxoethyl]-4-oxo-3-methyl-3,4-dihydroquinazolin-1-ium bromide 
• 1361513-19-0 4-acetyl-1-{2-[(methylamino)carbonyl]phenyl}-2-(4-nitrobenzoyl)-1H-pyrrole 
• 17730-53-9 4-Oxo-2-thioxo-1,3-dimethyl-1,2,3,4-tetrahydro-chinazolin 
• 22686-81-3 3-methyl-2-phenyl-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes

A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

N3-Alkylation during formation of quinazolin-4-ones from condensation of anthranilamides and orthoamides

Dimethylformamide dimethylacetal (DMFDMA) is widely used as a source of electrophilic one-carbon units at the formate oxidation level; however, electrophilic methylation with this reagent is previously unreported. Reaction of anthranilamide with DMFDMA at 150 °C for short periods gives mainly quinazolin-4-one. However, prolonged reaction with dimethylformamide di(primary-alkyl)acetals leads to subsequent alkylation at N3. 3-Substituted anthranilamides give 8-substituted 3-alkylquinazolin-4-ones. Condensation of anthranilamides with dimethylacetamide dimethylacetal provides 2,3-dimethylquinazolin-4-ones. In these reactions, the source of the N 3-alkyl group is the O-alkyl group of the orthoamides. By contrast, reaction with the more sterically crowded dimethylformamide di(isopropyl)acetal diverts the alkylation to the oxygen, giving 4-isopropoxyquinazolines, along with N3-methylquinazolin-4-ones where the methyl is derived from N-Me of the orthoamides. Reaction of anthranilamide with the highly sterically demanding dimethylformamide di(t-butyl)acetal gives largely quinazolin-4-one, whereas dimethylformamide di(neopentyl)acetal forms a mixture of quinazolin-4-one and N3-methylquinazolin-4-one. The observations are rationalised in terms of formation of intermediate cationic electrophiles (alkoxymethylidene-N,N-dimethylammonium) by thermal elimination of the corresponding alkoxide from the orthoamides. These are the first observations of orthoamides as direct alkylating agents.

Polycyclic N-heterocyclic compounds. Part 601): Reactions of 3-(2-cyanophenyl)quinazolin-4(3H)-ones with primary amines

The reaction of 3-(2-cyanophenyl)quinazolin-4(3H)-one with various primary alkylamines gave 3-alkylquinazolin-4(3H)-ones via an addition of the nucleophile, ring opening, and ring closure (ANRORC) mechanism. This type of reaction required hydroxy group fu

A Facile Synthesis of 3-Substituted 2-Cyanoqmnazolin-4(3H)-ones and 3-Alkyl-2-cyanothieno[3,2-d]pyrimidin-4(3H)-ones via 1,2,3-Dithiazoles

The reaction of methyl anthranilate with 4,5-dichloro-l,2,3-dithiazolium chloride (Appel's salt) in the presence of pyridine (2 equivalents) in dichloromethane at room temperature gave methyl N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)anthranilate (3a) (50% yield), which reacted with sterically less hindered primary alkylamines to give directly 3-alkyl-2-cyanoquinazolin-4(3H)-ones 5 in moderate to good yields. With tertbutylamine, N-(2-methoxycarbonylphenyl)iminocyanomethyl N-(tert-butyl) disulfide 7 and methyl 2-(N-cyanothioformamido)anthranilate (8) were isolated in 33% and 59% yields, respectively. The cyano group of quinazoline 5a (R = CH3) is readily displaced by various nucleophiles to give 2-substituted quinazolinones 11-19, which indicates that compounds 5 can be utilized as starting materials for the synthesis of new 2-substituted quinazolines. Similarly 3-alkyl-2-cyanothieno[3,2,-d]pyrimidin-4(3H)-ones 22 were prepared from methyl 3-[N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)]-2-thiophencarboxylate (21) in moderate to good yields.