22686-82-4

Usage

Uses

Used in Pharmaceutical Industry:
2,3-diphenylquinazolin-4(3H)-one is used as a lead compound for the development of new drugs due to its potential pharmacological activities, including antimicrobial, antifungal, and anti-inflammatory properties. Its structure serves as a promising scaffold for designing and synthesizing novel therapeutic agents.
Used in Antioxidant Applications:
2,3-diphenylquinazolin-4(3H)-one is used as an antioxidant, which may help in protecting cells from oxidative damage and could have implications for the treatment of various diseases associated with oxidative stress.
Used in Enzyme Inhibition:
2,3-diphenylquinazolin-4(3H)-one is used as an enzyme inhibitor, targeting specific enzymes that play a role in disease processes. Its ability to inhibit certain enzymes makes it a candidate for the development of drugs that can modulate enzyme activity for therapeutic purposes.

Upstream product

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• 4903-36-0 N-phenyl-benzimidoyl chloride 
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• 77796-30-6 4,5,6,7-tetrachloro-2',3'-diphenyl-spiro<1,3-benzodioxole-2,4'(3'H)-quinazoline> 
• 118-92-3 anthranilic acid 
• 62-53-3 aniline 
• 65-85-0 benzoic acid 
• 117193-95-0 3-azido-2,3-dihydro-2,3-diphenylisoindol-1-one 
• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 1663-61-2 triethoxymethylbenzene 
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Downstream Products

• 52458-01-2 4,4-di-naphthalen-1-yl-2-phenyl-4H-benzo[d][1,3]oxazine 
• 22706-60-1 2,4,4-Triphenyl-4H-3,1-benzoxazine 
• 62-53-3 aniline 

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.

Complementary Reactivity in Selective Radical Processes: Electrochemistry of Oxadiazolines to Quinazolinones

Electrochemistry has recently emerged as a sustainable approach for efficiently generating radical intermediates utilizing eco-friendly electric energy. An electrochemical process was developed to transform 1,2,4-oxadiazolines under mild conditions. The electrochemical N-O bond cleavage at a controlled oxidation potential led to the selective synthesis of quinazolinone derivatives that could not be obtained by photocatalytic radical processes, indicating complementary reactivities in radical processes. The electrochemical reaction pathways were fully revealed by density functional theory-based investigations.

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water

We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).

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

α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocyclesviadecarboxylative oxidative annulation reaction

A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include thein situgeneration of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.

Ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H)-ones: A convergent synthetic route to bouchardatine and sildenafil

A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra) in a highly convergent manner. This journal is

Generation of N-Centered Radicals via a Photocatalytic Energy Transfer: Remote Double Functionalization of Arenes Facilitated by Singlet Oxygen

An unprecedented approach to the generation of an N-centered radical via a photocatalytic energy-transfer process from readily available heterocyclic precursors is reported, which is distinctive of the previous electron transfer approaches. In combination with singlet oxygen, the in-situ-generated nitrogen radical from the oxadiazoline substrate in the presence of fac-Ir(ppy)3 undergoes a selective ipso addition to arenes to furnish remotely double-functionalized spiro-azalactam products. The mechanistic studies provide compelling evidence that the catalytic cycle selects the energy-transfer pathway. A concurrent activation of molecular oxygen to generate singlet oxygen by energy transfer is also rationalized. Furthermore, the occurrence of the electron transfer phenomenon is excluded on the basis of the negative driving forces for one-electron transfer between oxadiazoline and the excited state of fac-Ir(ppy)3 with a consideration of their redox potentials. The necessity of singlet oxygen as well as the photoactivated oxadiazoline substrate is clearly supported by a series of controlled experiments. Density functional studies have also been carried out to support these observations. The scope of substrates is explored by synthesizing diversely functionalized cyclohexadienone moieties in view of their utility in complex organic syntheses and as potential targets in pharmacology.

Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone

The invention discloses a method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone. According to the method, heteropolyacid ion liquid is taken as a catalyst, microwave heating and solvent-free synthesis technologies are utilized, and dihydroquinazolinone and quinazolinone derivatives are selectively synthesized through a 'one-pot-method' synthetic strategy with isatoic anhydride or derivatives of the isatoic anhydride, amine and aldehyde as raw materials. Compared with the prior art, the method has the multiple advantages that the efficiency is high, the costis low, environmental friendliness is realized, reaction selectivity is good, the product yield is high, selective synthesis can be realized, the catalyst is convenient to recover and apply, operationis easy, and industrial mass production is convenient, and the method is an environment-friendly efficient selective synthesis novel method and meets the environment-friendly and chemical developmentidea.

Tandem Oxidative Cyclocondensation towards 2,3-Disubstituted Quinazolinones in the Presence of [Bmim][BF4] and Iodine

The metal-free synthesis of 2-aryl-3-arylmethylquinazolin-4(3H)-one is achieved through ionic liquid mediated and I2-promoted tandem oxidative cyclocondensation of isatoic anhydrides with arylmethylamines as the common precursor for the 2-aryl