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Usage

Uses

Used in Pharmaceutical Development:
2,3-Dihydro-2-phenylquinazoline-4(1H)-one is used as a potential antiproliferative agent for the development of new pharmaceutical drugs. Its ability to inhibit cell proliferation makes it a candidate for the treatment of various diseases, including cancer.
Used in Enzyme Inhibition:
2,3-Dihydro-2-phenylquinazoline-4(1H)-one is used as an enzyme inhibitor, targeting specific enzymes that play a role in disease progression. By inhibiting these enzymes, the compound may help in the management and treatment of certain conditions.
Used in Medicinal Chemistry Research:
2,3-Dihydro-2-phenylquinazoline-4(1H)-one is used as a subject of study in medicinal chemistry, where researchers explore its potential applications and properties. Its unique structure and pharmacological activities make it an interesting compound for further research and development in drug discovery.

InChI:InChI=1/C14H12N2O/c17-14-11-8-4-5-9-12(11)15-13(16-14)10-6-2-1-3-7-10/h1-9,13,15H,(H,16,17)

Upstream product

• 17762-72-0 2-phenyl-tetrahydro-(2H)-1,3-oxazine 
• 28144-70-9 anthranilic acid amide 
• 16192-33-9 3-Methyl-2-phenyl-2,3-dihydrobenzothiazoline 
• 610-15-1 2-nitrobenzamide 
• 100-52-7 benzaldehyde 
• 118-48-9 isatoic anhydride 
• 758640-21-0 N-Benzylaniline 
• 2042-37-7 o-cyanobromobenzene 
• 31230-83-8 2-Phenylbenzothiazolin 
• 100-39-0 benzyl bromide 
• 100-53-8 phenylmethanethiol 
• 100-42-5 styrene 
• 100-46-9 benzylamine 
• 612-24-8 o-nitrobenzonitrile 

Downstream Products

• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 80478-01-9 1,3-diacetyl-2-phenyl-1,2,3,4-tetrahydroquinazolin-4-one 
• 100-52-7 benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 1044499-41-3 (R)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 1044499-42-4 (S)-2-cyclohexyl-2,3-dihydroquinazolin-4(1H)-one 
• 55661-71-7 2-phenyl-1,2,3, 4-tetrahydroquinazoline 
• 26060-01-5 3-allyl-2-phenylquinazolin-4(3H)-one 
• 67796-16-1 2-phenyl-3-n-butylquinazoline-4(3H)-one 
• 26060-02-6 2-phenyl-3-n-propylquinazoline-4(3H)-one 
• 939966-50-4 3-(4-methoxybenzyl)-2-phenyl-(3H)-quinazolin-4-one 
• 19857-37-5 3-benzyl-2-phenyl-3,4-dihydroquinazolin-4-one 

Relevant academic research and scientific papers

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Sustainable parts-per-million level catalysis with FeIII: One-pot cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water

A silica-supported iron complex has been identified as a highly active and reusable catalyst for the synthesis of medicinally important 2,3-dihydroquinazolin-4(1H)-ones. The catalyst was fully characterized by various spectroscopic analyses such as Fourie

Cu(II) complex-decorated hybrid nanomaterial: a retrievable catalyst for green synthesis of 2,3-dihydroquinazolin-4(1H)-ones

The significant stability of magnetic core and ? OH functional groups on the surface of silica-coated cobalt ferrite (CoFe2O4@SiO2) nanoparticles make it a good candidate for functionalization and catalytic application. In

β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one

β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.

An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols

An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.

Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.

Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.

Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles

A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.

Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions

A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.

Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide

A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.