4765-57-5

Usage

Chemical class

Quinazolinone

Derivative

2-(2-phenylethyl)quinazolin-4(1H)-one is a derivative of quinazoline.

Also known as

Phensuximide

Pharmaceutical applications

The compound has been investigated for its potential use in the treatment of epilepsy, Parkinson's disease, and neuropathic pain.

Anticonvulsant properties

2-(2-phenylethyl)quinazolin-4(1H)-one has demonstrated anticonvulsant properties in animal studies.

Research use

The compound has been used as a reference compound in research on antiepileptic drugs.

Chemical structure

The chemical structure of 2-(2-phenylethyl)quinazolin-4(1H)-one makes it an interesting target for further research in the field of neuroscience and drug development.

Upstream product

• 28144-70-9 anthranilic acid amide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 872998-62-4 C₈H₅BrN₂O 
• 91634-12-7 C₁₀H₈N₂O 
• 71-43-2 benzene 
• 104-54-1 3-Phenylpropenol 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 104-55-2 3-phenyl-propenal 
• 491-36-1 4-Hydroxyquinazoline 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 645-45-4 hydrocinnamic acid chloride 
• 104-53-0 3-phenyl-propionaldehyde 
• 80478-02-0 2-phenethyl-1,2,3,4-tetrahydroquinazolin-4-one 

Downstream Products

• 1233224-93-5 C₂₄H₁₉N₅O₃ 

Relevant academic research and scientific papers

Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones

In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.

Method for photocatalytic synthesis of quinazolinone

The invention discloses a method for photocatalytic synthesis of quinazolinone. Anthranilamide and aldehyde are used as raw materials, fluorescein is used as a photocatalyst, p-toluene sulfonic acid is used as an auxiliary catalyst, and the quinazolinone is obtained through photocatalytic reaction under the irradiation of visible light. The non-metal catalyst is used, so that the reaction cost is reduced; the reaction conditions are mild, and the reaction can be completed at room temperature; and the method is simple to operate, short in reaction time, simple in post-treatment, high in product yield and more environment-friendly. The method not only has high academic value, but also has a certain industrialization prospect.

Method for preparing quinazolinone from enol

The invention discloses a method for preparing a quinazolinone derivative from enol. According to the method, a relatively inexpensive ruthenium complex is used as a catalyst in a reaction to catalyzea microwave reaction of commercial and easily-available 2-aminobenzamide with enol for the preparation of quinazolinone. Compared with conventional synthesis methods for quinazolinone of the same kind, the method of the invention has the following advantages: no alkali is used in the reaction process; clean and non-toxic tetrahydrofuran is used as a reaction solvent; hydrogen is automatically transferred, and the atom economy of the reaction is high; and the by-product of the invention is only water.

Auto-Tandem Catalysis with Ruthenium: From o-Aminobenzamides and Allylic Alcohols to Quinazolinones via Redox Isomerization/Acceptorless Dehydrogenation

A strategy for the synthesis of quinazolinones via Ru-catalyzed redox isomerization/acceptorless dehydrogenation was proposed and accomplished. In the presence of a commercially available [(p-cymene)Cl2]2, a range of desirable products were obtained with o-aminobenzamides and allylic alcohols as starting materials in moderate to high yields. This strategy is attractive due to high atom efficiency, and minimal consumption of chemicals and energy. (Figure presented.).

The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru-clusters/Ceria Catalyst

Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru-clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H2O is generated as the only by-product. A series of quinazolinones with aromatic or non-aromatic substituents can be obtained in yields of up to 99 %. The Ru-clusters/ceria can be reused at least four times. The analysis of the E-factor (environmental impact factor) for the synthesis of 2-ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.

Quinazolinone compound preparation method

The present invention relates to a quinazolinone compound preparation method, wherein a quinazolinone-based compound is prepared by using 2-aminobenzamide, olefin and carbon monoxide as reaction substrates and using tetrahydrofuran as a solvent under the catalysis effect of a ruthenium loaded metal oxide. The reaction process comprises: adding tetrahydrofuran, 2-aminobenzamide, olefin and a catalyst into a pressure container, inflating with carbon monoxide, sealing, stirring, and carrying out a reaction for not less than 0.5 h at a reaction temperature of not lower than 120 DEG C, wherein thecatalyst is easily separated from the reaction system after the reaction, and can be recycled multiple times, and the yield of the quinazolinone-based compound is up to 100%.

Method for synthesizing quinazolinone from anthranilamide and unsaturated aldehyde

The invention discloses a method for synthesizing quinazolinone from anthranilamide and unsaturated aldehyde. The method comprises the steps: adding the quinazolinone, a transition metal catalyst, methylbenzene and the unsaturated adhehyde in a reaction container, making a reaction mixture react under 110 to 120 DEG C for 10 to 12 hours and cooling to room temperature; then separating to obtain atarget compound. According to the method disclosed by the invention, the anthranilamide and the unsaturated aldehyde which are easy to obtain are utilized as beginning raw materials, only water is generated as a byproduct in reaction, and reaction atom economy is high; thus, the reaction meets a green chemical requirement and has a wide development prospect.

Method for synthesis of quinazolinone derivative

The invention discloses a method for synthesis of quinazolinone; the method comprises the steps of starting from o-aminobenzamide, taking water as a solvent, carrying out a ring-enlargement reaction with benzaldehyde, to generate a dihydroquinazolinone intermediate, and then under participation of a metal iridium complex, dehydrogenating to obtain the quinazolinone derivative; the reaction shows three remarkable advantages: 1) the reaction is carried out in an aqueous solution so as to reduce use of a large amount of organic solvents, and water is a cheap, green and safe solvent; 2) the reaction avoids use of highly toxic oxidants, so as to avoid damage to the environment; and 3) hydrogen gas generated from the reaction is a by-product, and has no environmental pollution; therefore, the reaction accords with the requirements of green chemistry, and has broad prospects for development.

Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

A photoredox-mediated Minisci C-H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system.

Substitute quinazolines derivative with Aurora kinase inhibitory activity and application thereof

The invention discloses a substitute quinazolines derivative with Aurora kinase inhibitory activity and application thereof. The substitute quinazolines derivative is a compound as shown in a formula (I) and a formula (II),or its pharmaceutically acceptable salt, hydrate, solvate, polymorphic substance,tautomer or prodrug. A medicine composition includes one or more of the compound as shown in the formula (I) and the formula (II),or its pharmaceutically acceptable salt, hydrate, solvate, polymorphic substance,tautomer or prodrug. The application of the substitute quinazolines derivative with the Aurora kinase inhibitory activity comprises application of the compound as shown in the formula (I) and the formula (II),or its pharmaceutically acceptable salt, hydrate, solvate, polymorphic substance,tautomer or prodrug to preparation of medicine for inhibiting Aurora kinase; or application of the compound as shown in the formula (I) and the formula (II), or its pharmaceutically acceptable salt, hydrate, solvate, polymorphic substance,tautomer or prodrug to preparation of medicine for treating and/or preventing and/or relieving and/or conducting auxiliary treating and/or treating proliferative diseases; or application of the compound as shown in the formula (I) and the formula (II),or its pharmaceutically acceptable salt, hydrate, solvate, polymorphic substance,tautomer or prodrug to preparation of medicine for resisting to tumor. The series compound has good inhibitory activity on Aurora kinase.